Silicone coating composition, its method of manufacture, and articles

Abstract

Provided is a condensation-reaction-curable silicone coating agent composition which contains, as a main component, a hydrolysable-group-containing organosiloxane mixture and also contains a curing catalyst, in which the hydrolysable-group-containing organosiloxane mixture contains an organotrisiloxane compound having a specified molecular structure in which there is at least one non-substituted, halogen-substituted or alkyl-substituted phenyl group in the molecule thereof and at least four hydrolysable groups are contained at molecule chain both ends thereof and an organodisiloxane compound having a specified structure in which there are at least two non-substituted, halogen-substituted or alkyl-substituted phenyl groups on one silicon atom in the molecule thereof and at least two hydrolysable groups are contained on the other silicon atom in the molecule thereof, and the organotrisiloxane compound and the organodisiloxane compound are contained in the hydrolysable-group-containing organosiloxane mixture at a specified blend ratio. The silicone coating agent composition has excellent storage stability although no organic solvent is contained, and can be cured rapidly at ambient temperature after being applied on a substrate to provide a cured coating film having excellent transparency, adhesiveness and the like, having excellent conformability to the shape of the substrate upon the bending of the substrate, and capable of preventing the corrosion of the substrate.

Description

[Technical field]

[0001] The present invention relates to a moisture-curable room-temperature curable silicone coating composition that crosslinks and cures by hydrolysis and condensation reaction with atmospheric moisture (water) at room temperature (23°C ± 10°C), and in particular to a silicone coating composition used for protecting and sealing electric and electronic parts, structural parts, etc. The silicone coating composition of the present invention has excellent storage stability, and after being applied to various substrates, it cures quickly at room temperature to give a cured coating film that is excellent in transparency, flexibility (ability to follow the bending of the substrate), adhesion (adhesion to the substrate), low gas permeability, etc., and therefore can be used as a silicone coating composition (so-called silicone conformal coating composition) that can impart various functionalities to various substrates, such as surface protection, water repellency, rust prevention, water resistance, weather resistance, chemical resistance, and contamination resistance. [Background technology]

[0002] Unlike other common hydrocarbon organic resins, silicone resins (organopolysiloxane resins) are excellent in heat resistance, weather resistance, water resistance, flame retardancy, etc., and can form cured coatings with high hardness on the surface. Therefore, curable silicone rubber compositions (silicone elastomer compositions) having crosslinkable groups such as alkoxy groups and silanol groups bonded to silicon atoms in the molecule, and silicone resin-based resins (polyorganosilsesquioxane resins having a three-dimensional network structure, etc.) are widely used in applications and fields such as surface protection materials for various substrates, heat-resistant paints, weather-resistant paints, water repellents, and various binders. In particular, silicone resins are used for conformal coating of electronic substrates such as home appliances and electronic components because of their good heat resistance and electrical insulation. In addition, by devising resin compositions, it has become possible to create coating compositions that do not require dilution with organic solvents, and coating agents that are excellent in terms of VOC (volatile organic compound) issues and safety have been put on the market. However, typical silicone rubber-based or silicone resin-based coating compositions have a low protective effect on electrode metals (particularly silver electrodes) against corrosive gases such as hydrogen sulfide, and a solution to this problem has been desired.

[0003] In the past, in order to reduce metal corrosion caused by corrosive gases such as hydrogen sulfide, it was necessary to use acrylic resin-based and urethane resin-based coating agents, but such organic resin coating materials are generally used in a diluted state with organic solvents, which poses problems with VOCs and safety.In addition, there are limitations to the range of use (operating temperature, insulation properties) of acrylic and urethane coating agents due to problems with heat resistance and electrical properties. For the reasons described above, there has been a demand for a solventless silicone coating agent which, in addition to having excellent heat resistance and electrical properties, also has excellent ability to prevent metal corrosion caused by corrosive gases such as hydrogen sulfide.

[0004] The present invention is a silicone coating material that forms a hard cured film after curing, and as such a silicone coating composition, a so-called silicone varnish solution, which is a curable silicone resin having a terminal silanol group and an average molecular weight of about 3,000 to 2,000,000 dissolved in an organic solvent such as toluene or xylene, has been widely used. By using this, a coating excellent in surface hardness, adhesion, heat resistance, weather resistance, water resistance, etc. can be obtained, but since it uses an organic solvent that has a large environmental load as an essential component and utilizes a dehydration condensation crosslinking reaction between silanol groups, it generally requires long-term heating and curing at 150°C or higher to form a coating.

[0005] In response to this, there is a demand for one-part, solventless, room temperature curing silicone coating agent compositions that do not contain organic solvents, can be cured at room temperature, and have excellent storage stability. For this purpose, the use of relatively low molecular weight silicone alkoxy oligomers obtained by partial (co)hydrolysis and condensation of organoalkoxysilanes has been examined. At the same time, active research has been conducted into curing catalysts that effectively promote the moisture-induced hydrolysis reaction and dealcoholization condensation reaction of these silicone alkoxy oligomers to form crosslinked coatings through siloxane bonds, and the following technologies have been proposed (Patent Documents 1 and 2: JP-A-60-233164, JP Patent No. 4110402). However, in both techniques, the resulting cured coating is rigid and has poor flexibility, and is therefore poor at conforming to the bending of the substrate, and furthermore, it is not possible to prevent metal corrosion caused by hydrogen sulfide.

[0006] On the other hand, examples of techniques for preventing corrosion of base metals by sulfurous corrosive gases in solventless silicone compositions include techniques for adding metal powders such as silver and copper to the composition and reducing corrosion of the base metal by sacrificial corrosion of the metal powder (Patent Documents 3 and 4: Japanese Patent No. 4114037 and Japanese Patent No. 4530137), and techniques for reducing corrosion of base metals by organic additives (Patent Document 5: Japanese Patent No. 6418115). Both are excellent techniques, but they are means for neutralizing corrosive gas species that penetrate into the silicone coating by reactions inside the coating, and depending on the type of corrosive gas, the effect is insufficient. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Japanese Patent Application Publication No. 60-233164 [Patent Document 2] Patent No. 4110402 [Patent Document 3] Patent No. 4114037 [Patent Document 4] Patent No. 4530137 [Patent Document 5] Patent No. 6418115 Summary of the Invention [Problem to be solved by the invention]

[0008] The present invention has been made to solve the above-mentioned problems, and aims to provide a silicone coating composition that does not contain an organic solvent, does not impair the inherent properties of a curable organosilicon compound, has excellent storage stability as a coating composition, cures quickly at room temperature (23°C±10°C, the same below) after application to a substrate, and can give a cured coating that is excellent in transparency, adhesion, etc., has excellent conformability (flexibility) to bending of the substrate, and has low gas permeability, thereby preventing corrosion of the substrate, particularly reducing sulfurization caused by hydrogen sulfide, a sulfurous gas. In particular, in the protection and sealing of electric / electronic parts, structural parts, etc., the glass transition temperature (Tg) of the cured coating is lowered while maintaining the corrosion prevention properties of the coating, thereby widening the usable temperature range of the sealing parts, and a silicone coating composition (silicone conformal coating composition) that can be used in a wide temperature range, especially on the low temperature side, and Its manufacturing method, The object is to provide an article which is sealed, coated, fixed or adhered with the cured product of said silicone coating composition. [Means for solving the problem]

[0009] As a result of intensive research conducted by the present inventors in order to achieve the above-mentioned object, it has been found that a hydrolyzable group-containing organosiloxane mixture is used as the base agent, and is a combination of a specific blend ratio of an organotrisiloxane compound having a specific molecular structure, the organotrisiloxane compound having at least one unsubstituted, halogen-substituted or alkyl-substituted phenyl group in the molecule and containing at least four, and preferably four to six, hydrolyzable groups at both molecular chain terminals, and an organodisiloxane compound having a specific molecular structure, the organodisiloxane compound having at least two unsubstituted, halogen-substituted or alkyl-substituted phenyl groups on the same silicon atom in the molecule and containing at least two, and preferably two or three, hydrolyzable groups on the other same silicon atom in the molecule. The present invention has been completed based on the findings that, by using a condensation reaction-curing silicone coating composition containing the above, it is possible to obtain a cured coating which exhibits excellent storage stability in a sealed environment (air-blocking environment), and which cures rapidly in an open atmosphere by hydrolysis and condensation reactions caused by moisture (humidity) in the air, and which has excellent transparency, adhesion, etc., and which has excellent conformability (flexibility) to bending of the substrate, and which has low gas permeability, thereby making it possible to reduce sulfurization of the cured coating caused by hydrogen sulfide, and furthermore, it is possible to lower the glass transition temperature (Tg) of the cured product, and therefore it is possible to obtain a silicone coating composition which can be used over a wide temperature range, particularly on the low temperature side.

[0010] That is, the present invention provides the following silicone coating composition and Its manufacturing method, The cured product of the composition provides an article that is sealed, coated, fixed or adhered. [1] (A) 100 parts by mass of a hydrolyzable group-containing organosiloxane mixture comprising (A-1) 20 to 95 parts by mass of a hydrolyzable group-containing organotrisiloxane compound represented by the following general formula (1-1) and (A-2) 80 to 5 parts by mass of a hydrolyzable group-containing organodisiloxane compound represented by the following general formula (1-2) (the total of components (A-1) and (A-2) is 100 parts by mass), [ka] [ka] (In each formula, R 1 , R 3 , R 4 are each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, each X is independently at least one hydrolyzable group selected from an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, and a is independently 0 or 1 for each silicon atom to which it is bonded. (B) Curing catalyst: 0.01~10 parts by mass A silicone coating composition comprising: [2] In the above general formula (1-1), R 3 The silicone coating composition according to [1], wherein R is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group. [3] The silicone coating composition according to [1] or [2], wherein in the above general formulas (1-1) and (1-2), X is a methoxy group, an ethoxy group, an isopropenyloxy group, or a ketoxime group, respectively. [4] The silicone coating agent composition according to any one of [1] to [3] further contains, other than the components (A-1) and (A-2), a hydrolyzable organosilane compound represented by the following general formula (2) and / or a partial hydrolysis condensate thereof (C) in an amount of 0.1 to 100 parts by mass per 100 parts by mass of the component (A). (R 1 ) a Si(X) (4-a) (2) (In the formula, R 1 , X, a are the same as above.) [5] The silicone coating composition according to any one of [1] to [4], which does not contain an organic solvent. [6] under General formula (2) (R 1 ) aSi(X) (4-a) (2) (In the formula, R 1 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms , X represents independently at least one hydrolyzable group selected from an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group, and a ketoxime group; , a is 0 or 1 .) and a hydrolyzable organosilane compound represented by the following general formula (3): [ka] (In the formula, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group; , R 3 teeth An unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms. .) and a diorganosilanediol represented by the formula: in the presence of a condensation reaction catalyst. Combination reaction By this, the component (A-1) is represented by the following general formula (1-1): [ka] (In the formula, R 1 、R 2 、R 3 , X, a are the same as above.) preparing a hydrolyzable group-containing organotrisiloxane compound represented by the formula: , above A hydrolyzable organosilane compound represented by the general formula (2) and a hydrolyzable organosilane compound represented by the following general formula (4): [ka] (In the formula, R 2 is the same as above , R 4 teeth An unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms. .) and a triorganohydroxysilane represented by the formula: in the presence of a condensation reaction catalyst. Condensation Reaction By this, the component (A-2) is represented by the following general formula (1-2): [ka] (In the formula, R 1 、R 2 、R 4 , X, a are the same as above.) A step of preparing a hydrolyzable group-containing organodisiloxane compound represented by the formula: characterized in thatThe silicone coating composition according to any one of [1] to [5]. Manufacturing method . [7] [1]~[ 5 13. An article sealed, coated, fixed or adhered with a cured product of the silicone coating composition according to any one of claims 1 to 12. Effect of the Invention

[0011] According to the present invention, it is possible to provide a silicone coating composition, particularly a silicone conformal coating composition, which has excellent storage stability, can be applied to a substrate even without containing an organic solvent, and after application, quickly forms a cured coating at room temperature, and the cured coating has excellent transparency, adhesion, etc., excellent conformability (flexibility) to bending of the substrate, and has low gas permeability, thereby preventing corrosion of the substrate, in particular reducing sulfurization due to hydrogen sulfide, and furthermore, it is possible to lower the glass transition temperature (Tg) of the cured product, and therefore it is possible to provide a silicone coating composition, particularly a silicone conformal coating composition, which can be used over a wide temperature range, particularly on the low temperature side. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

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

[0013] [Component (A)] Component (A) is a hydrolyzable group-containing organosiloxane mixture containing specific proportions of (A-1) a hydrolyzable group-containing organotrisiloxane compound represented by general formula (1-1) described below, and (A-2) a hydrolyzable group-containing organodisiloxane compound represented by general formula (1-2) described below. The hydrolyzable group-containing organosiloxane mixture containing components (A-1) and (A-2) undergoes rapid crosslinking and curing through a hydrolysis and condensation reaction in the presence of the curing catalyst for component (B) described below in the presence of atmospheric moisture (moisture) at room temperature (23°C ± 10°C, the same applies hereinafter) to give a cured coating that is excellent in transparency, adhesion, etc., has excellent conformability to the bending of the substrate (flexibility), and has reduced gas permeability.

[0014] [Component (A-1)] Component (A-1) is the main component of the silicone coating composition of the present invention, and is an organotrisiloxane compound of a specific molecular structure represented by the following general formula (1-1), which has at least one, and preferably 1 to 4, unsubstituted, halogen-substituted or alkyl-substituted phenyl groups in the molecule, and at least 4, and preferably 4 to 6 hydrolyzable groups in the molecule (on each of the silicon atoms at both ends of the molecular chain). [ka] (In the formula, R 1 , R 3 are each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, each X is independently at least one hydrolyzable group selected from an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, and a is independently 0 or 1 for each silicon atom to which it is bonded.

[0015] In the above formula (1-1), R 1 , R 3are each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and examples thereof include linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, nonyl, and decyl groups; linear, branched or cyclic alkenyl groups having 2 to 10 carbon atoms, such as vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, hexenyl, and cyclohexenyl groups; phenyl, tolyl, xylyl, mesityl, naphthyl, and the like. and halogen-substituted monovalent hydrocarbon groups in which some of the hydrogen atoms of these groups have been substituted with halogen atoms or the like, such as a chloromethyl group, a 2-bromoethyl group, a 3,3,3-trifluoropropyl group, a 3,3,4,4,5,5,5-heptafluoropentyl group, a 2,3,3-trifluoro-2-chlorocyclobutyl group, a 3,4-dibromo-1-chlorohexyl group, a difluoromonochlorovinyl group, a 2-iodocyclohexenyl group, a chlorophenyl group, a perchlorophenyl group, a fluorophenyl group, a perfluorophenyl group, a 2,2,2-trifluorotolyl group, or a 2,4-dibromobenzyl group.

[0016] Of these, R 1 As the alkyl group, a methyl group, an ethyl group, a propyl group, a vinyl group, and a phenyl group are preferable. 2 As will be explained in the section above, when low gas permeability of the resulting cured coating is important, unsubstituted, halogen-substituted or alkyl-substituted phenyl groups are preferred, but various other monovalent organic groups can be selected for reasons of designing the curing speed due to the hydrolysis and condensation reaction of the composition of the present invention.

[0017] R 3From the viewpoint of reducing the gas permeability of the resulting cured coating, the alkyl group is preferably an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, such as a phenyl group, a tolyl group, a xylyl group, a chlorophenyl group, a perchlorophenyl group, a fluorophenyl group, a perfluorophenyl group or a 2,2,2-trifluorotolyl group. Also, R 3 By using a monovalent hydrocarbon group other than the above-mentioned unsubstituted, halogen-substituted, or alkyl-substituted phenyl group as R, the Tg of the cured coating can be controlled, and the R can be adjusted to match the desired low gas permeability and Tg. 3 Among these, alkyl groups, allyl groups and fluoroalkyl groups are preferred because the resulting cured coating has good releasability and water repellency.

[0018] In the above formula (1-1), R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, such as a phenyl group, a tolyl group, a xylyl group, a chlorophenyl group, a perchlorophenyl group, a fluorophenyl group, a perfluorophenyl group, a 2,2,2-trifluorotolyl group, etc. A phenyl group is preferred. The hydrolyzable group-containing organotrisiloxane compound of formula (1-1) of component (A-1) must have at least one unsubstituted, halogen-substituted or alkyl-substituted phenyl group per molecule (on a silicon atom not at the molecular chain terminal). When low gas permeability is important, it is preferable that there are two (i.e., R 2 and R 3 It is preferred that the phenyl groups have unsubstituted, halogen-substituted or alkyl-substituted phenyl groups. It is the unsubstituted, halogen-substituted or alkyl-substituted phenyl groups that reduce the gas permeability of the cured coating; if a hydrolyzable group-containing organotrisiloxane compound does not have an unsubstituted, halogen-substituted or alkyl-substituted phenyl group in the molecule, the resulting cured coating will have high gas permeability and will not be able to reduce corrosion of the base metal due to corrosive gases.

[0019] In the above formula (1-1), each X is independently at least one hydrolyzable group selected from an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group, and a ketoxime group. Specific examples of X include alkoxy groups having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, and tert-butoxy group; alkoxy-substituted alkoxy groups having 2 to 4 carbon atoms, such as a methoxy-substituted methoxy group, a methoxy-substituted ethoxy group, an ethoxy-substituted methoxy group, and an ethoxy-substituted ethoxy group; alkenyloxy groups having 2 to 4 carbon atoms, such as a vinyloxy group, an allyloxy group, a propenyloxy group, an isopropenyloxy group, and a butenyloxy group; aryloxy groups having 6 to 10 carbon atoms, such as a phenyloxy group; acyloxy groups having 2 to 4 carbon atoms, such as an acetoxy group and a propionoxy group; and ketoxime groups having 3 to 6 carbon atoms, such as a dimethylketoxime group, a methylethylketoxime group, and a diethylketoxime group. Preferred are a methoxy group, an ethoxy group, an isopropenyloxy group, a methyl ethyl ketoxime group, and the like.

[0020] In the above formula (1-1), a is independently 0 or 1 for each silicon atom to which it is bonded, and is preferably 1. The hydrolyzable group-containing organotrisiloxane compound of component (A-1) has at least 4, preferably 4 to 6, and more preferably 4 hydrolyzable groups X in each molecule (on each of the silicon atoms at both ends of the molecular chain) in the above formula (1-1).

[0021] Specific examples of the hydrolyzable group-containing organotrisiloxane compound represented by formula (1-1) include the compounds shown below. [ka] [ka]

[0022] The hydrolyzable group-containing organotrisiloxane compound of component (A-1) represented by the above general formula (1-1) contains the above-mentioned hydrolyzable group X or R as a monovalent hydrocarbon group bonded to a silicon atom represented by the following general formula (2): 1 and a hydrolyzable group X; and the above-mentioned R 2 and R 3 and a diorganosilanediol having at least one, preferably two, unsubstituted, halogen-substituted or alkyl-substituted phenyl groups in the molecule, in the presence of a condensation reaction catalyst under conventionally known conditions, thereby easily producing the compound. (R 1 ) a Si(X) (4-a) (2) [ka] (In each formula, R 1 , R 2 , R 3 , X, a are the same as above.)

[0023] Specific examples of the hydrolyzable organosilane compound represented by the above formula (2) include vinyltrimethoxysilane, phenyltrimethoxysilane, methyltrimethoxysilane, vinyltriisopropenoxysilane, phenyltriisopropenoxysilane, and methyltriisopropenoxysilane.

[0024] Specific examples of the diorganosilanediol (diorganodihydroxysilane) represented by the above formula (3) include diphenylsilanediol, methylphenylsilanediol, and the like.

[0025] The reaction ratio of the hydrolyzable organosilane compound represented by formula (2) and the diorganosilanediol represented by formula (3) is preferably such that the molar ratio of the silanol groups derived from the diorganosilanediol represented by formula (3) to the hydrolyzable organosilane compound represented by formula (2) is 2 or less, but in order to reduce the residual silanol groups in the reaction product, the molar ratio is more preferably 0.5 to 1.5. If the reaction product contains a large amount of residual silanol groups derived from the raw material diorganosilanediol represented by formula (3), the subsequent curing reaction rate of the composition may be reduced.

[0026] Examples of the condensation reaction catalyst used in the above reaction include organometallic catalysts such as organotitanate compounds, titanium chelate compounds, aluminum chelate compounds, and organozirconium compounds, and non-metallic catalysts such as guanidyl compounds such as tetramethylguanidylpropyltrimethoxysilane. The amount of the condensation reaction catalyst added may be an amount sufficient for the condensation reaction between the hydrolyzable organosilane compound represented by formula (2) and the diorganosilanediol represented by formula (3) to proceed at room temperature or under heating, and is preferably 0.01 to 10 parts by mass, particularly preferably 0.1 to 5 parts by mass, per 100 parts by mass of the total of the hydrolyzable organosilane compound represented by formula (2) and the diorganosilanediol represented by formula (3).

[0027] The reaction conditions are preferably a temperature of 0 to 150° C., particularly about 25 to 100° C., and a time of 30 seconds to 5 hours, particularly about 1 to 120 minutes, and further preferably about 10 to 60 minutes. In addition, it is preferable to carry out the reaction while removing the compound HX (alcohol, acetone, etc.) that is eliminated or produced as a by-product by the condensation reaction, and it is also possible to humidify the mixture as necessary.

[0028] In the silicone coating composition of the present invention, the hydrolyzable group-containing organotrisiloxane compound (A-1) constituting component (A) can use either a single compound, or a combination of two or more different compounds.

[0029] [Component (A-2)] The (A-2) component is the main component of the silicone coating composition of the present invention together with the (A-1) component, and is an organodisiloxane compound of a specific molecular structure represented by the following general formula (1-2), which has at least two, preferably two or three, unsubstituted, halogen-substituted or alkyl-substituted phenyl groups on the same silicon atom in the molecule, and at least two, preferably two or three hydrolyzable groups on the other same silicon atom in the molecule. By combining the (A-2) component with the (A-1) component at a specific blending ratio, it is possible to lower the glass transition temperature (Tg) of the target cured product. By lowering the Tg of the cured coating, the flexibility of the material can be maintained over a wider temperature range, especially on the low temperature side, which is a very important characteristic from the viewpoint of expanding the temperature range of the intended sealing part.

[0030] [ka] (In the formula, R 1 , R 2 , X, a are the same as above. R 4 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms.

[0031] In the above formula (1-2), R 1 , R 2 , X and a are R in the above formula (1-1) 1 , R 2 , X, and a can be exemplified. 1 , R 2 , X and a are R in formula (1-1) 1 , R 2 , X, and a may be the same as or different from each other.

[0032] In the above formula (1-2), R 4 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and R in formula (1-1) 1 , R 3Examples of the alkyl group include those exemplified in the above. Preferred are alkyl groups or alkenyl groups, and more preferred are methyl groups, ethyl groups, propyl groups, trifluoropropyl groups, and vinyl groups.

[0033] The hydrolyzable group-containing organodisiloxane compound of component (A-2) represented by formula (1-2) must have at least two, preferably two or three, more preferably two unsubstituted, halogen-substituted or alkyl-substituted phenyl groups on the same silicon atom in the molecule (on a silicon atom that does not have a hydrolyzable group).The unsubstituted, halogen-substituted or alkyl-substituted phenyl groups reduce the gas permeability of the cured coating, and if a hydrolyzable group-containing organodisiloxane compound does not have an unsubstituted, halogen-substituted or alkyl-substituted phenyl group in the molecule, the resulting cured coating will have high gas permeability and will not be able to reduce corrosion of the base metal due to corrosive gases. The hydrolyzable group-containing organodisiloxane compound of formula (1-2), component (A-2), when used in combination with component (A-1), can form a cured coating that retains low gas permeability and has a lower glass transition temperature (Tg) than a coating obtained by curing a composition of component (A-1) alone, and that has flexibility over a wider temperature range on the low temperature side.

[0034] The hydrolyzable group-containing organodisiloxane compound of component (A-2) has at least two, preferably two or three, and more preferably two hydrolyzable groups X on the same silicon atom (one end of the molecular chain) in one molecule in the above formula (1-2).As the hydrolyzable group X, a group suitable for achieving the desired curing speed and storage properties can be selected.

[0035] Specific examples of the hydrolyzable group-containing organodisiloxane compound represented by formula (1-2) include the compounds shown below. [ka] [ka]

[0036] The hydrolyzable group-containing organodisiloxane compound of component (A-2) represented by the above general formula (1-2) contains the above-mentioned hydrolyzable group X or R as a monovalent hydrocarbon group bonded to a silicon atom represented by the following general formula (2): 1 and a hydrolyzable group X; and a hydrolyzable organosilane compound having the above-mentioned R 2 Two and R 4 It can be easily produced by subjecting a triorganohydroxysilane having at least two unsubstituted, halogen-substituted or alkyl-substituted phenyl groups in the molecule having one phenyl group to a de-HX condensation reaction in the presence of a condensation reaction catalyst under conventionally known conditions. (R 1 ) a Si(X) (4-a) (2) [ka] (In each formula, R 1 , R 2 , R 4 , X, a are the same as above.)

[0037] Examples of the hydrolyzable organosilane compound represented by the above formula (2) include the same compounds as those used in the production of the hydrolyzable group-containing organotrisiloxane compound represented by the above formula (1-1). A specific example of the triorganohydroxysilane (triorganosilanol) represented by the above formula (4) is methyldiphenylsilanol.

[0038] The reaction ratio of the hydrolyzable organosilane compound represented by formula (2) and the triorganohydroxysilane represented by formula (4) is preferably 2 or less in the molar ratio of the hydrolyzable organosilane compound represented by formula (2) to the triorganohydroxysilane represented by formula (4), but in order to reduce the amount of triorganohydroxysilane represented by formula (4) remaining in the reaction product, the molar ratio is more preferably 0.5 or more and 1.5 or less. If the amount of the raw material triorganohydroxysilane represented by formula (4) remaining in the reaction product (i.e., the amount of remaining silanol groups) is large, the curing reaction rate of the subsequent composition may be reduced.

[0039] Examples of the condensation reaction catalyst used in the above reaction include organometallic catalysts such as organotitanate compounds, titanium chelate compounds, aluminum chelate compounds, and organozirconium compounds, and non-metallic catalysts such as guanidyl compounds such as tetramethylguanidylpropyltrimethoxysilane. The amount of the condensation reaction catalyst added may be an amount sufficient for the condensation reaction between the hydrolyzable organosilane compound represented by formula (2) and the triorganohydroxysilane represented by formula (4) to proceed at room temperature or under heating, and is preferably 0.01 to 10 parts by mass, particularly preferably 0.1 to 5 parts by mass, per 100 parts by mass of the total of the hydrolyzable organosilane compound represented by formula (2) and the triorganohydroxysilane represented by formula (4).

[0040] The reaction conditions are preferably a temperature of 0 to 150° C., particularly about 25 to 100° C., and a time of 30 seconds to 5 hours, particularly about 1 to 120 minutes, and further preferably about 10 to 60 minutes. In addition, it is preferable to carry out the reaction while removing the compound HX (alcohol, acetone, etc.) that is eliminated or produced as a by-product by the condensation reaction, and it is also possible to humidify the mixture as necessary.

[0041] In the silicone coating composition of the present invention, the hydrolyzable group-containing organodisiloxane compound (A-2) constituting component (A) can use either a single compound, or a combination of two or more different compounds.

[0042] In the hydrolyzable group-containing organosiloxane mixture of component (A), the mass ratio of component (A-1) to component (A-2) is 20:80 to 95:5, preferably 40:60 to 95:5, and more preferably 30:70 to 80:20. If the amount of component (A-1) is greater than the above range (if the amount of component (A-2) is less than the above range), the hardness of the cured film may be too high, which may cause cracks in the coating film, and if the amount of component (A-1) is less than the above range (if the amount of component (A-2) is greater than the above range), the film may not be cured sufficiently.

[0043] In the silicone coating agent composition of the present invention, there is no restriction on the order of mixing components (A-1) and (A-2) which constitute the hydrolyzable group-containing organosiloxane mixture of component (A). Components (A-1) and (A-2) may be mixed in advance to prepare a mixture of component (A), and then this mixture of component (A) may be mixed with component (B) to prepare the composition of the present invention. Alternatively, either component (A-1) or component (A-2) may be mixed with component (B), and the remaining either component (A-1) or component (A-2) may be mixed with this mixture to prepare the composition of the present invention.

[0044] [(B) Component] The curing catalyst for component (B) is a condensation reaction catalyst necessary for component (A), which is a hydrolyzable group-containing organosiloxane mixture containing specific proportions of (A-1) a hydrolyzable group-containing organotrisiloxane compound represented by general formula (1-1) above, and (A-2) a hydrolyzable group-containing organodisiloxane compound represented by general formula (1-2) above, to undergo a hydrolysis and condensation reaction with moisture (water) in the air to rapidly produce a cured coating, and an appropriate catalyst is selected according to the reactivity of the hydrolyzable group X selected in the above general formula (1-1) of component (A-1) and the above general formula (1-2) of component (A-2).

[0045] Examples of such condensation reaction catalysts include hydroxides, chlorides, oxides, and basic metal salts of alkali metals or alkaline earth metals. Specific examples include hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, chlorides of alkaline earth metals such as calcium chloride and magnesium chloride, oxides of alkaline earth metals such as calcium oxide and magnesium oxide, and basic metal salts such as basic zinc carbonate and basic magnesium carbonate.

[0046] Other condensation reaction catalysts that can be used include aluminum chelate compounds, organic titanium compounds, organic zirconium compounds, organic tin compounds, aminoalkylalkoxysilanes, and ammonium salts. Examples of aluminum chelate compounds include aluminum (ethylacetoacetate) diisopropylate, aluminum di(ethylacetoacetate) isopropylate, aluminum tris(ethylacetoacetate), aluminum (acetylacetonate) diisopropylate, aluminum di(acetylacetonate) isopropylate, aluminum tris(acetylacetonate), aluminum bis(ethylacetoacetate) mono(acetylacetonate), and aluminum bis(acetylacetonate) mono(ethylacetoacetate). Examples of the organic titanium compound include tetraisopropoxytitanium, tetra-n-butoxytitanium, and tetrakis(2-ethylhexoxy)titanium. Examples of the organic zirconium compound include tetraisopropoxyzirconium, tetra-n-butoxyzirconium, and tetrakis(2-ethylhexoxy)zirconium. Examples of organotin compounds include tin salts of carboxylic acids such as dioctyltin, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctoate, stannous octoate, stannous naphthenate, stannous oleate, stannous isobutyrate, stannous linoleate, stannous stearate, stannous benzoate, stannous naphthoate, stannous laurate, o-stannous thymate, stannous β-benzoylpropionate, stannous crotonate, stannous tropate, stannous p-bromobenzoate, stannous palmitoleate, stannous cinnamate, and stannous phenylacetate. Examples of aminoalkylalkoxysilanes include tetramethylguanidylpropyltrimethoxysilane, γ-aminopropyltrimethylmethoxysilane, γ-aminopropyltriethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, and γ-(dimethylamino)propyltrimethoxysilane. Examples of ammonium salts include salts of acids and amines. Examples of acids include acetic acid and formic acid, and examples of amines include allylamine, 2-ethylhexylamine, 3-ethoxypropylamine, diisobutylamine, 3-diethylaminopropylamine, di-2-ethylhexylamine, dibutylaminopropylamine, tri-n-octylamine, tert-butylamine, sec-butylamine, propylamine, and 3-methoxypropylamine.

[0047] The amount of the curing catalyst of component (B) to be blended is 0.01 to 10 parts by mass, and particularly preferably 0.02 to 5 parts by mass, per 100 parts by mass of the hydrolyzable group-containing organosiloxane mixture of component (A) (i.e., the total of components (A-1) and (A-2)), in order to ensure that the reaction proceeds well and the resulting silicone coating composition has good curability.

[0048] [(C) component] The silicone coating composition of the present invention may further contain, as an optional component, the hydrolyzable organosilane compound represented by the above formula (2) and / or its partial hydrolysis condensate (C), which is the same as that used as a raw material in the production of the above components (A-1) and (A-2), in addition to the above components (A-1), (A-2), as necessary. The incorporation of the component (C) provides the effect of improving the storage stability of the composition and controlling the curing time. When the hydrolyzable organosilane compound represented by the above formula (2) is reacted with the diorganosilanediol represented by the above formula (3) or the triorganohydroxysilane represented by the above formula (4) to obtain the component (A-1) or the component (A-2), the hydrolyzable organosilane compound represented by the formula (2) may be reacted in an excess amount, and the surplus hydrolyzable organosilane compound represented by the formula (2) and / or its partial hydrolysis condensate after the reaction may be used as is.

[0049] The content of component (C) should be 100 parts by mass or less (0 to 100 parts by mass) per 100 parts by mass of component (A), and when added, it is preferably 0.1 to 100 parts by mass, and more preferably about 0.1 to 50 parts by mass. If the amount of component (C) is too large, it may cause thermal deterioration or discoloration of the cured coating.

[0050] [Other ingredients] The silicone coating composition of the present invention may further contain small amounts of various additives, such as plasticizers, release agents, flame retardants, antioxidants, ultraviolet absorbers, and pigments and dyes, such as titanium dioxide, carbon black, or iron oxide, as necessary, within the scope of the present invention.Furthermore, fumed silica, silica aerogel, silica gel, and reinforcing silica fillers obtained by treating these with organic silanes, organic siloxanes, or organic silazanes, as well as asbestos, crushed fused quartz, aluminum oxide, aluminum silicate, zirconium silicate, zinc oxide, talc, diatomaceous earth, mica, calcium carbonate, clay, zirconia, glass, sand, graphite, barium sulfate, zinc sulfate, aluminum powder, sawdust, cork, fluorocarbon polymer powder, silicone rubber powder, silicone resin powder, and other fillers may also be contained within the scope of the present invention.

[0051] Furthermore, an organic solvent may be blended as necessary, but in consideration of VOC and safety, it is preferable that the composition contains no organic solvent or contains only a small amount of organic solvent as long as the composition has a viscosity that can be used in the process.

[0052] In producing the silicone coating composition of the present invention, it is sufficient to simply mix the above-mentioned (A-1), (A-2), and (B) components in the prescribed amounts, and in this case, the temperature during mixing is not limited, but there is no need to perform any particular operation such as heating, and the composition can be easily obtained by simply stirring and mixing at room temperature for 10 minutes or more, preferably 10 to 60 minutes. Note that, when mixing, it is preferable to carry out this process under a nitrogen atmosphere in order to prevent hydrolyzable groups such as alkoxy groups from being hydrolyzed due to the inclusion of moisture. Incidentally, components (A-1) and (A-2) may be prepared separately and then mixed together. Alternatively, a mixture of diorganosilanediol represented by formula (3) above and triorganohydroxysilane represented by formula (4) above may be simultaneously subjected to a condensation reaction with the hydrolyzable organosilane compound represented by formula (2) above to prepare a mixture containing components (A-1) and (A-2).

[0053] In this manner, the silicone coating composition of the present invention can provide articles that are sealed, coated, fixed or adhered with the cured product of the composition. The silicone coating composition of the present invention can be applied to various metal substrates, wood, stone, mortar boards, slate boards, roofing tiles, concrete, glass, ceramics, plastic products, organic resin coating products, etc., by a conventionally known method, and cured to form a coating film. In this case, specific examples of the application method include brush application, spray application, immersion, flow coater, knife coater, spin coater, etc., and on-site application is also possible. The amount of application varies depending on the type of substrate and the purpose of coating, but generally, the thickness of the coating film after curing is in the range of 0.1 to 300 μm, and preferably in the range of 1 to 200 μm.

[0054] The curing conditions for the silicone coating composition of the present invention are not particularly limited, but since the composition cures due to moisture in the air to form a coating, it will dry (reach a tack-free state) when left at room temperature to 80°C for about 1 minute to 2 hours, and the curing reaction can be completed by leaving it for a further several hours to several days.

[0055] In this manner, the silicone coating composition of the present invention can provide articles that are sealed, coated, fixed or adhered with the cured product of the composition. EXAMPLES

[0056] The present invention will be specifically described below with reference to Preparation Examples, Examples, and Comparative Examples, but the present invention is not limited to the following Examples. Note that room temperature means 23° C. In addition, % in the table is mass %.

[0057] [Preparation Example] Ingredient (A-1) (A-1-1) Diphenylsilanediol (16.2 g), vinyltrimethoxysilane (25 g), and a titanium chelate catalyst (0.2 g, Orgatix TC-401, manufactured by Matsumoto Fine Chemical Co., Ltd.) were added to a 100 ml flask and reacted for 60 minutes at 100° C. While removing the generated methanol with a nitrogen gas flow, the excess vinyltrimethoxysilane was further removed with a nitrogen gas flow to obtain an organotrisiloxane compound (A-1-1) represented by the following formula. [ka]

[0058] (A-1-2) Diphenylsilanediol (16.2 g), phenyltrimethoxysilane (25 g), and titanium chelate catalyst (0.2 g, TC-401) were added to a 100 ml flask and reacted at 100°C for 60 minutes while removing the generated methanol with a nitrogen gas flow. The excess phenyltrimethoxysilane was then removed by heating under reduced pressure to obtain organotrisiloxane compound (A-1-2) represented by the following formula. [ka]

[0059] (A-1-3) Diphenylsilanediol (16.2 g), vinyltriisopropenoxysilane (25 g), and tetramethylguanidylpropyltrimethoxysilane (0.2 g) were added to a 100 ml flask and reacted at 100° C. for 60 minutes while removing the generated acetone with a nitrogen gas flow. The excess vinyltriisopropenoxysilane was then removed by heating under reduced pressure to obtain the organotrisiloxane compound (A-1-3) represented by the following formula. [ka]

[0060] Ingredient (A-2) (A-2-1) Methyldiphenylsilanol (29 g), vinyltrimethoxysilane (25 g), and titanium chelate catalyst (0.2 g, TC-401) were added to a 100 ml flask and reacted for 60 minutes at 100°C. The methanol generated was removed with a nitrogen gas flow, and then the excess vinyltrimethoxysilane was removed with a nitrogen gas flow to obtain the organodisiloxane compound (A-2-1) represented by the following formula. [ka]

[0061] (A-2-2) Methyldiphenylsilanol (29 g), phenyltrimethoxysilane (25 g), and titanium chelate catalyst (0.2 g, TC-401) were added to a 100 ml flask and reacted at 100°C for 60 minutes while removing the generated methanol with a nitrogen gas flow. The excess phenyltrimethoxysilane was then removed by heating under reduced pressure to obtain organodisiloxane compound (A-2-2) represented by the following formula. [ka]

[0062] (A-2-3) Methyldiphenylsilanol (29 g), vinyltriisopropenoxysilane (25 g), and tetramethylguanidylpropyltrimethoxysilane (0.2 g) were added to a 100 ml flask and reacted at 100° C. for 60 minutes while removing the generated acetone with a nitrogen gas flow. The excess vinyltriisopropenoxysilane was then removed by heating under reduced pressure to obtain an organodisiloxane compound (A-2-3) represented by the following formula. [ka]

[0063] (A-1) Ingredients (for comparison) (a-1) Dimethylsilanediol (12.3 g, some of which was dimerized), methyltrimethoxysilane (20 g), and titanium chelate catalyst (0.2 g, TC-401) were added to a 100 ml flask and reacted at 100°C for 60 minutes. The methanol that was generated was removed with a nitrogen gas flow, and then the excess methyltrimethoxysilane was removed with a nitrogen gas flow to obtain organotrisiloxane compound (a-1) represented by the following formula. [ka]

[0064] (A-2) Ingredients (for comparison) (a-2) Trimethylsilanol (13.5 g), methyltrimethoxysilane (20 g), and titanium chelate catalyst (0.2 g, TC-401) were added to a 100 ml flask and reacted for 60 minutes at 100°C. The methanol that was generated was removed with a nitrogen gas flow, and then the excess methyltrimethoxysilane was removed with a nitrogen gas flow, yielding organodisiloxane compound (a-2) represented by the following formula. [ka]

[0065] [Examples 1 to 6, Comparative Examples 1 to 9] The components shown in Tables 1 to 3 were mixed in the amounts shown in Tables 1 to 3 in a 10 ml glass cup and stirred at room temperature for 10 minutes to mix uniformly, to obtain silicone coating compositions. Examples 1 to 6 and Comparative Examples 1 to 8 did not contain a solvent component. The appearance and properties of the obtained silicone coating compositions were visually inspected and are shown in Tables 1 to 3. The silicone coating composition obtained above was cured under the curing conditions of 23°C / 50% Rh for 7 days to form a coating having a thickness of about 2 mm. The appearance and properties of the obtained cured product (cured coating) were confirmed by visual inspection and touch, and are shown in Tables 1 to 3. Regarding the properties of the cured product, when the cured coating was pressed with a finger at 23°C and no change was observed in the surface shape of the coating, it was judged to be a "hard coating", and when an indentation was made on the surface of the coating by the finger, it was judged to be a "soft coating".

[0066] The raw materials used in addition to the component (A) obtained in the above Preparation Example are shown below. (B) Component (B-1) Tin catalyst: U-830 (manufactured by Nitto Kasei Co., Ltd., dioctyl tin) (B-2) Amine catalyst: Tetramethylguanidylpropyltrimethoxysilane

[0067] (A) Ingredients (for comparison) (a-3) A solvent-based coating agent, Humiseal (registered trademark)-1B66NS, mainly composed of acrylic resin, was prepared. The solid content was 35% by mass (solvent content 65% by mass), but in order to apply a thin film, it was diluted 2x with an additional solvent (diluent: Humiseal (registered trademark) thinner 901).

[0068] [Table 1]

[0069] [Table 2]

[0070] [Table 3]

[0071] Next, the silicone coating agent compositions of Examples 1 to 6 and Comparative Examples 1 to 9 were evaluated for cured product appearance, tack-free time, glass transition point, corrosion prevention test, and flexibility. These results are shown in Tables 4 and 5.

[0072] (Appearance of cured product) The coating film prepared in the tack-free time evaluation described below and cured on an aluminum petri dish was visually evaluated for transparency and degree of coloration.

[0073] (Tuck free time) Approximately 0.20 g of the silicone coating composition was placed on an aluminum petri dish and spread over a square area of ​​approximately 2 cm x 2 cm, and the adhesion / curing time of the composition surface was evaluated by touch with the fingers.

[0074] (Glass transition temperature (Tg)) The glass transition temperature (Tg) was measured from the heat absorption characteristics using a Mettler DSC. About 0.03 g of the silicone coating composition was poured into an aluminum pan and cured under the conditions of 23°C / 50% Rh×7 days to obtain a sample. The temperature rise conditions were −60°C to 150°C, and the temperature rise rate was 10°C / min.

[0075] (Corrosion prevention test) About 0.08g of each material (silicone coating composition) was spread on the surface of a silver-plated aluminum plate in a square shape of about 2cm x 2cm so that the cured film was about 200μm, and cured under the curing conditions of 23℃ / 50%Rh×7 days, and the corrosion state of the silver-plated surface was observed over time (initial, 1 day, 3 days, 7 days, 14 days) using a hydrogen sulfide gas corrosion tester. The corrosion conditions were as follows: Hydrogen sulfide concentration: 2 ppm Temperature: 23℃ Humidity: 50%RH The silver-plated surface was observed before and after the corrosion test, and it was determined that corrosion had occurred when the initial silver luster changed (turned black or gray).

[0076] (flexibility) After completing the above corrosion prevention test, the coated silver-plated aluminum sheet (having a cured film of the silicone coating composition) was bent at an angle of 90° at 23°C with the cured film facing outward, and an evaluation was made as to whether the coating layer could conform to the substrate without cracking.

[0077] [Table 4]

[0078] [Table 5]

[0079] (result) From the above results, it was confirmed that the silicone coating agent composition of the present invention is solvent-free and has excellent curability and transparency at room temperature, and that the cured coating film obtained by curing the composition has excellent transparency, is effective in preventing corrosion of metal substrates from corrosive gases, has excellent substrate conformability (flexibility), and has a lower glass transition point, allowing for a wide usable temperature range.

Claims

1. (A) 100 parts by mass of a hydrolyzable group-containing organosiloxane mixture comprising (A-1) 20 to 95 parts by mass of a hydrolyzable group-containing organotrisiloxane compound represented by the following general formula (1-1), and (A-2) 80 to 5 parts by mass of a hydrolyzable group-containing organodisiloxane compound represented by the following general formula (1-2) (the total of components (A-1) and (A-2) is 100 parts by mass), 【Chemistry 1】 【Chemistry 2】 (In each formula, R 1 , R 3 , R 4 are each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, each X is independently at least one hydrolyzable group selected from an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, and a is independently 0 or 1 for each silicon atom to which it is bonded. (B) Curing catalyst: 0.01 to 10 parts by mass A silicone coating composition comprising:

2. In the above general formula (1-1), R 3 2. The silicone coating composition according to claim 1, wherein is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group.

3. 3. The silicone coating composition according to claim 1, wherein in the general formulas (1-1) and (1-2), X is a methoxy group, an ethoxy group, an isopropenyloxy group, or a ketoxime group.

4. The silicone coating composition according to any one of claims 1 to 3, further comprising, other than components (A-1) and (A-2), a hydrolyzable organosilane compound represented by the following general formula (2) and / or a partial hydrolysis condensate thereof (C), in an amount of 0.1 to 100 parts by mass per 100 parts by mass of component (A): (R 1 ) a Si(X) (4-a) (2) (In the formula, R 1 , X, and a are the same as above.)

5. The silicone coating composition according to any one of claims 1 to 4, which does not contain an organic solvent.

6. The following general formula (2) (R 1 ) a Si(X) (4-a) (2) (In the formula, R 1 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X is independently at least one hydrolyzable group selected from an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group, and a ketoxime group, and a is 0 or 1. and a hydrolyzable organosilane compound represented by the following general formula (3): 【Chemistry 3】 (In the formula, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group; R 3 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms. and a diorganosilanediol represented by the following general formula (1-1) of component (A-1) by subjecting the diorganosilanediol to a condensation reaction in the presence of a condensation reaction catalyst: 【Chemistry 5】 (In the formula, R 1 , R 2 , R 3 , X, and a are the same as above.) preparing a hydrolyzable group-containing organotrisiloxane compound represented by the formula: A hydrolyzable organosilane compound represented by the above general formula (2) and a hydrolyzable organosilane compound represented by the following general formula (4) 【Chemistry 4】 (In the formula, R 2 is the same as above, and R 4 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms. and a triorganohydroxysilane represented by the following general formula (1-2) of component (A-2) by subjecting the triorganohydroxysilane represented by the following general formula (1-2) in the presence of a condensation reaction catalyst. 【Chemistry 6】 (In the formula, R 1 , R 2 , R 4 , X, and a are the same as above.) A step of preparing a hydrolyzable group-containing organodisiloxane compound represented by the formula: The method for producing the silicone coating composition according to any one of claims 1 to 5, comprising the steps of:

7. An article that is sealed, coated, fixed or adhered with a cured product of the silicone coating composition according to any one of claims 1 to 5.

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