JPH05222198A - Silicone compound, vinyl copolymer therewith and coating composition made by using it - Google Patents

Abstract

PURPOSE:To improve the weatherability, acid resistance, solvent resistance, stain resistance, smoothness, etc., by adding a compound having carbon-to-carbon unsaturated bond(s) onto the Si-H group of a specified hydrosilicone compound. CONSTITUTION:A compound having carbon-to-carbon unsaturated bond (s) is added onto the Si-H group of a hydrosilicone compound which has structures of formulas I and II (wherein R<6> is H, 1-18C linear or branched alkyl or phenyl, provided that at least one of R<6> is H; and R<2> is 1-18C linear or branched alkyl or phenyl), has a terminal group having an R<2>O-structure when bonded to the Si terminal or having an R<2>-structure when bonded to the O terminal, and has a ratio of R<1> to R<2> of (0.8 to 10):1 to give a silicone compound which has structures of formulas III and IV (wherein R<1> is R<6> or a group of formula V, VI or VII; R<3> is H or methyl; Q is ether or ester; R<4> is 2-10C alkylene; and R<5> is R<2> and contains at least one residue of group of formula V or VI in terms of statistical probability) in the molecular structure, a number-average molecular weight of 800 to 250,000, and a ratio of R<1> to R<2> of (0.8 to 10):1.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a silicone compound useful as a raw material for paints, coating agents, sealing agents, adhesives, etc., which are excellent in weather resistance, acid resistance, solvent resistance, stain resistance, smoothness, etc. , A copolymer thereof, and a coating composition using the same.

[0002]

2. Description of the Related Art A vinyl polymer having an alkoxysilyl group at a molecular end or a side chain and a coating composition using the same are disclosed, for example, in JP-A-54-36395 and JP-A-54-40893. JP-A-54-123129
It is well known in Japanese Patent Publication No.

[0003]

[Problems to be Solved by the Invention] However, recently,
In the fields of construction, automobiles, metal coatings, etc., there is a demand for coating materials having further excellent performance in terms of performance such as weather resistance, acid resistance, solvent resistance, stain resistance and smoothness.

[0004]

The present inventors have solved the above problems by creating a silicone compound having a specific structure having a polymerizable double bond, and a copolymer thereof, and applying it to a coating material. They have found that they can be solved, and have completed the present invention. That is, the present invention has both the structures represented by the following general formulas (A) and (B) in the molecular structure (1),
(2) When bonded to silicon as an end group, R ² —O—
And the case of binding to oxygen has a structure of R ² — (R ²
Is a linear or branched alkyl group having 1 to 18 carbon atoms, or a phenyl group), (3) number average molecular weight 800 to 20,000
0, and (4) R ¹ / R ² ratio is 0.8 to 10, a silicone-based compound [compound-I],

[0005]

[Chemical 4]

And (1) in the molecular structure, the following general formula (C)
And (D), and (2) has a structure of R ² —O— when bound to silicon as an end group and R ² — when bound to oxygen (R ² is a carbon atom). Number 1-18
Linear or branched alkyl group, or phenyl group),
(3) A vinyl-based copolymer having a number average molecular weight of 1,000 to 200,000 having a silicone-based functional group having an R ¹ / R ² ratio of 0.8 to 10 in at least one side chain [copolymer] Combined-I],

[0007]

[Chemical 5]

A coating composition comprising the above vinyl-based copolymer as a main component. [Compound-
The silicone compound represented by the formula [I] is disclosed in, for example, Japanese Patent Application No.
As described in Japanese Patent Application No. 12718, Japanese Patent Application No. 2-12720 and Japanese Patent Application No. 3-43382, a structure represented by the following general formulas (E) and (F) in the molecular structure. R ² —O— when bonded to the silicon terminal as an end group and R ² — (R
² has the same structure as the above R ² ) and has a R ¹ / R ² ratio of 0.8 to 10 in which the Si-H group contained in the hydrosilicone compound [Compound-II] has carbon- It can be obtained by adding a carbon unsaturated bond compound (hydrosilylation reaction).

[0009]

[Chemical 6]

This [Compound-II] is hydrolyzed and polycondensed by reacting trichlorosilane or a trichlorosilane / organotrichlorosilane mixture with water in a solvent such as dioxane as described in the above-mentioned application. ,
It is then obtained by reacting with alcohol. The structure of [Compound-II] thus obtained is as follows. A typical example of the case where R ⁶ is hydrogen and R ² is a methyl group (Me) with a relatively low molecular weight is as follows: , (H) and (Q).

[0011]

[Chemical 7]

[0012]

[Chemical 8]

[0013]

[Chemical 9]

Examples of the carbon-carbon unsaturated bond compound to be added to this [compound-II] include, for example, propylene, 1-butene, 1-hexene, 1-octene, isobutene, 5-methyl-1-butene. Olefins such as 2-hexene and cyclohexene, allyl acetates such as allyl acetate, allyl propionate, allyl 2-ethylhexanoate and allyl benzoate, allyl methyl ether, allyl ethyl ether, allyl-n-hexyl ether, allyl Allyl ethers such as cyclohexyl ether, allyl-2-ethylhexyl ether, allyl phenyl ether, allyl glycidyl ether, etc. Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, (meth) acrylic acid-2 -Ethylhexyl, (meth) a (Meth) acrylic acid esters such as cyclohexyl acrylate and phenyl (meth) acrylate, carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl stearate and vinyl benzoate, methyl vinyl ether, ethyl vinyl ether , Vinyl ethers such as butyl vinyl ether, isobutyl vinyl ether, and cyclohexyl vinyl ether; and other carbon-carbon unsaturated bond compounds such as styrene, (meth) acrylonitrile, and crotonic acid esters.

Of these, terminal olefins such as 1-hexene and 1-octene, allyl esters and allyl ethers are preferable from the viewpoint of reactivity. Furthermore, examples of the carbon-carbon unsaturated bond compound for introducing an epoxy group into the silicone compound represented by [Compound-I] include carbon-carbon unsaturated bond such as allyl glycidyl ether and glycidyl (meth) acrylate. And a compound having both epoxy in one molecule. Of these, allyl glycidyl ether is preferably used. Further, as the carbon-carbon unsaturated bond compound for introducing the polymerizable double bond into the silicone compound represented by [Compound-I], for example, allyl (meth) acrylate,
Two or more double bond groups such as diallyl ether, diallyl phthalate (meth) acrylic acid vinyl, vinyl crotonic acid vinyl, cinnamic acid vinyl, ethylene glycol di (meth) acrylic acid ester, butylene glycol di (meth) acrylic acid ester A compound which has both in one molecule is mentioned. Of these, allyl (meth) acrylate is particularly preferable.

In the reaction of [Compound-II] of the present invention with the unsaturated bond compound, it is preferable to use a platinum group VIII catalyst. Examples of the Group VIII platinum-based catalyst include platinum simple substance, chloroplatinic acid, alcohol-modified chloroplatinic acid, platinum chloride-olefin complex, solid platinum supported on a carrier such as alumina and silica, and rhodium-olefin complex. For example, a Group VIII metal compound selected from cobalt, palladium and nickel is effectively used. The amount used is usually 1 to 100 with respect to the reaction product.
An amount of 0 ppm is used.

This hydrosylation reaction is carried out at 50 to 150
At a temperature of ° C a reaction time of 1 to 5 hours is achieved. When the reaction temperature is 50 ° C. or lower, the reaction rate becomes slow, which is not practical. Further, if the reaction temperature is 150 ° C. or higher, some high molecular weight products are generated and a gelling reaction occurs, which is not preferable. In the present invention, the molar ratio at the time of reacting [Compound-II] with the carbon-carbon unsaturated bond compound varies depending on the target reaction product, but is usually unsaturated with respect to 1 mol of Si-H groups. The binding compound is preferably in the range of 0.1 to 50 mol.

A solvent may be used in this reaction.
The solvent used is preferably a solvent that dissolves both the ladder-type hydrosilicone compound and the unsaturated bond compound. Usually, an organic solvent such as toluene or xylene is used. When a solvent is used, it is preferable to use 0.1 to 10 parts by weight with respect to 1 part by weight of the raw material used in the reaction.

The silicone compound [Compound-I] thus obtained has a cyclic silicone structure and / or a ladder-type silicone structure, a hydrolyzable alkoxysilyl group in the molecule, and It has a polymerizable double bond, an epoxy group, or a polymerizable double bond and an epoxy group, and is useful as a coating material, a coating material, a sealing material, and an adhesive material.

Having this polymerizable double bond [Compound-
I] is another polymerizable vinyl monomer copolymerizable therewith.
A vinyl-based copolymer [copolymer-I] having a residue of [compound-I] on the side chain is formed by copolymerization with the above. As the vinyl monomers to be copolymerized, it is possible to use, for example, the carbon-carbon unsaturated bond compound used in the above hydrosilation.
In particular, methyl (meth) acrylate, ethyl (meth) acrylate, -n-butyl (meth) acrylate, tert-butyl (meth) acrylate, hexyl (meth) acrylate,
Cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, phenyl (meth) acrylate, glycidyl (meth) acrylate, (meth)
2-hydroxyethyl acrylate, -3- (trimethoxysilyl) propyl (meth) acrylate, -3- (methyldimethoxysilyl) propyl (meth) acrylate,
(Meth) acrylic acid esters such as 3- (triethoxysilyl) propyl (meth) acrylate, isobornyl (meth) acrylate, (meth) acrylic acid, styrene and the like are preferably used.

Upon copolymerization, solution polymerization using an organic solvent in the presence of a polymerization initiator such as a peroxide or an azo compound is preferably used in a conventional manner. As the solvent, aromatic hydrocarbons such as benzene, toluene and xylene, esters such as ethyl acetate, butyl acetate and 2-ethylhexyl acetate, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone are usually used. It is also possible to use chain transfer agents such as mercaptan compounds and halogenated hydrocarbons.

The polymerization temperature varies depending on the type and amount of the polymerization initiator, but is usually selected from the range of room temperature to 150 ° C. The molecular weight of the obtained copolymer can be controlled by the types and amounts of the initiator and the chain transfer agent and the polymerization temperature, and is selected from the range of the number average molecular weight of 1,000 to 200,000.

The vinyl copolymer thus obtained has a specific silicone structure and a hydrolyzable alkoxysilyl group in at least one side chain, and also has an epoxy group if necessary. It is possible to heat cure, moisture cure, catalyst cure, etc.
It is a novel copolymer useful as a raw material for a ring agent and an adhesive.

When the resin having a specific structure obtained by the present invention is applied to a coating material, it is diluted with an aprotic solvent if necessary and then applied and cured. Upon curing, it is preferable to use an accelerating catalyst. Typical examples of such a curing catalyst include, for example, monomethyltin triacetate, dimethyltin diacetate, dibutyltin diacetate, dibutyltin di2-ethylhexanoate, dibutyltin dilaurate, diphenyltin. Dioctate, bis (dibutyltin monolaurate)
Tin compounds such as sulfide, monobutyltin dilaurate hydrochloride, tin 2-ethylhexanoate and dibutyltin oxide, zinc hexanoate, zinc 2-ethylhexanoate, zinc acetylacetonate, bis (zinc monoacetoacetate) )
Zinc compounds such as oxide, bis (zinc monoacetate) oxide, zinc dibenzoylmethane, lead hexanoate, lead 2-ethylhexanoate, lead acetylacetonate, etc., diisopropoxy bis ( Ethyl acetoacetate
Titanium), a titanium chelate compound such as diisopropoxy bis (acetylacetate) titanate or diisopropoxy bis (acetylacetone) titanate, diisopropylate ethylacetoacetate aluminum, Tris (ethylacetate) aluminum, tris (n-propylacetoacetate) aluminum,
Tris (isopropylacetoacetate) aluminum, tris (n-butylacetoacetate) aluminum, tris (acetylacetonate) aluminum, tris (ethylacetonate) aluminum, diisopropylethylethylacetonate aluminum, monoacetylacetate. Naat bis (ethylacetonate) aluminum, monoethylacetoacetate bis (acetylacetonate) aluminum, tris (isopropylate)
Aluminum chelate compounds such as aluminum, tris (sec-butyrate) aluminum, diisopropyl mono-sec-ptoxy aluminum or tris acetylacetone aluminum, tetrakis (acetylacetone) zirconium, tetrakis (n-propylacetoacetate) zirconium Zirconium compounds such as tetrakis (acetylacetonate) zirconium or tetrakis (ethylacetoacetate) zirconium, triethylamine, tributylamine, N, N,
N ', N'-trimethylethylenediamine, ethylenediamine, diethylenetriamine, diazabicyclooctane, dimer acid polyamide polyamine, isophoronediamine, xylylenediamine, diaminodiphenylmethane, phthalic anhydride, tetrahydrophthalic anhydride, pyromellitic anhydride, anhydrous Examples of the epoxy curing agent include trimellitic acid, phenol novolac, polymercaptan, polysulfide, and 2-methyl-4-ethylimidazole.

These catalysts may be appropriately mixed and used. The addition amount of the catalyst is usually 0.005% to 5 with respect to the resin.
It is selected from the range of weight%. The curing temperature depends on the nature of the object to be coated,
It can be freely set according to the purpose of coating, but generally, it may be selected in the range of natural drying at atmospheric temperature to bake hardening at about 220 ° C. It is needless to say that an additive such as an antioxidant, a light stabilizer, a viscosity controlling agent, a pigment for coloring, a metal powder such as an aluminum paste or the like can be added, if necessary, when forming a coating material.

[0026]

EXAMPLES The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the examples. The NMR analysis in the examples is JMX PMX.
60Si, infrared absorption spectrum (IR) used JASCO Corporation FT / IR-5300. The molecular weight is measured by gel permeation chromatography (GPC).
In the production example 1, Toso-TSK gel G5000HXL + G2500HXL, and in the examples Shodex KF-805 + KF-804 + K.
A column system of F-802 was used.

The coating film performance was evaluated according to the following method. 1) Mitsuzawa: JIS K5400-7.6 (60)
°) ◯: Specular glossiness = 85% or more 2) Surface smoothness: Surface roughness profile measuring device "Surfcom-5"
54AD "(manufactured by Tokyo Seimitsu Co., Ltd.) Surface property (good) ○>△> × (poor) 3) Gel fraction: The cured coating film is immersed in acetone at 20 ° C.
X Coating weight residual rate (%) after standing for 24 hours 4) Pencil hardness: JIS K5400-8.4.1 (Scratch evaluation) 5) Adhesion: JIS K5400-8.5.2.
○: 10 to 8 points, △: 6 to 4 points, ×: 2 to 0 points 6) Flexibility: JIS K5400-8.1 ○:
2mmφ pass, △: 3-6mmφ pass x: 8mmφ
Above 7) Contamination resistance: JIS K5400-8.10.
◯: No change, Δ: Minor change x: Significant change 8) Acid resistance: JIS K5400-8.22 9) Alkali resistance: JIS K5400-8.21 (5
% NaOH aqueous solution) 10) Solvent resistance: JIS K5400-8.24 (toluene) 11) Weather resistance: ASTM G-53 ◯: 2500
Gloss retention after time exposure = 95% or more x: Gloss retention after exposure to 2500 hours = 90% or less

[0028]

[Production Example 1] Synthesis of [Compound-II] 1200 g of dioxane and 1 mol of trichlorosilane were charged and stirred in a 2-liter four-necked flask equipped with a thermometer, a stirring rotor and a cooling tube. 18g water and 1 dioxane
A dropping funnel containing 8 g was attached to the 4-neck flask,
The solution was added dropwise while maintaining the temperature at 25 to 30 ° C. 3 more after dropping
After continuing stirring for 0 minutes, a dropping funnel containing 3 mol of ethanol was attached and dropping was performed while maintaining the temperature at 25 to 30 ° C.
Then, the mixture was stirred for another 120 minutes. Remove the reaction solution,
When the solvent was completely distilled off under reduced pressure below about 60 ° C, 7
9.3 g of low-viscosity silicone compound was obtained. This liquid was dissolved in chloroform, and this solution was added to gel permeation solution.
The molecular weight was measured by ion chromatography (hereinafter abbreviated as GPC method). As a result, a number average molecular weight (hereinafter, abbreviated as MN) 840, a weight average molecular weight (hereinafter, MW)
1600). Si- by ¹ H-NMR
H / OC ₂ H ₅ was about 1.2. Also, this silicone
1H was measured by adding hydrogen chloride compound to 2N-NaOH and measuring the hydrogen gas generated.
Hydrogen gas of mmol / g was generated.

[0029]

Example I-1 Synthesis of [Compound-I] A 200 ml four-necked flask equipped with a thermometer, a stirring rotor, a cooling tube, and a nitrogen supply introduction tube was charged with isopropanol containing 8% chloroplatinic acid. Solution 0.32 g, allyl methacrylate 3.41 g, allyl glycidyl ether 27.69 g, and toluene 50.8 g were charged. In addition, the silicone compound (19.) obtained in Production Example 1 was added to the dropping funnel.
9 g was put and attached to the above 4-necked flask. A small amount (about 5 ml / min) of nitrogen was poured, and the mixture was stirred and heated to raise the temperature. When the temperature inside the flask was raised to 70 ° C, the silicone
The entire amount of the compound was added while maintaining the temperature at 80 to 85 ° C. After completion of dropping, the mixture was stirred at a temperature of 80 to 85 ° C. for 3 hours. After the reaction is completed, the reaction solution is subjected to gas chromatography.
When analyzed by, the reaction rate of allyl methacrylate was 70
%, And the reaction rate of acrylic glycidyl ether was 77%.

When the solvent was distilled off from the reaction solution under reduced pressure at 50 ° C. or lower, 40.7 g of a pale yellow transparent liquid was obtained. When the molecular weight of this liquid was measured by the GPC method, MN1
It was 900. When this liquid was added to 2N-NaOH and the residual Si-H was measured, the reaction rate of Si-H was 76%. Further, in the IR analysis (infrared absorption spectrum), there was absorption of a carboxylic acid ester at 1720 cm ⁻¹ and absorption of a vinyl group at 1640 cm ⁻¹ . The IR spectrum is shown in FIG.

[0031]

Example I-2 Synthesis of [Compound-I] Platinum black was prepared by thoroughly replacing the inside of a 200 ml four-necked flask equipped with a thermometer, a stirring rotor, a cooling tube, and a nitrogen supply introduction tube with nitrogen. 0.5g was put, and then Production Example 1
Silicon compound of 19.2 g, 1-hexene 16.9
g, allyl methacrylate 4.85 g, toluene 40.9
g mixture was added. Start stirring and heating, 80 ~ 8
The temperature was raised to 5 ° C. The temperature was kept at 80 to 85 ° C. and stirred for 3 hours. The reaction solution was taken out and filtered to remove platinum black, and then the solvent was completely distilled off under reduced pressure of about 60 ° C. to obtain 30.8.
g of recovered material was obtained. By gas chromatography of the reaction liquid, the reaction rate of 1-hexene was 57%, the reaction rate of allyl methacrylate was 90%, and the reaction rate of Si—H was 73%.
N was 1700.

[0032]

Example I-3 Synthesis of [Compound-I] In a device similar to that of Example I-1, 0.10 g of isopropanol solution containing 8% of chloroplatinic acid and allyl acetate 7.5.
g, 8.3 g of the silicone compound obtained in Production Example 1, and 15.8 g of xylene were charged, and the mixture was stirred at a temperature of 80 to 85 ° C. for 2 hours. After that, 6.3 g of allyl methacrylate was added dropwise and reacted at 80 to 85 ° C. for 2 hours. The reaction solution is about 45
When the solvent was distilled off under reduced pressure at ° C, 15.2 g of a recovered product was obtained. As a result of gas chromatography analysis of the reaction liquid, the reaction rate of allyl acetate was 95% and the reaction rate of allyl methacrylate was 19%. When the molecular weight was measured by the GPC method, MN260
It was 0. The reaction rate of Si-H was 85%.

¹ H-NMR analysis result, 5.4 to 6.4 p
CH ₂ = C ¹ -group in pm is Si in 0.5 to 1.1 ppm
It can be seen that there is a —CH ₂ — group. This ¹ H-NMR spectrum is shown in FIG. IR analysis result, 1750 cm
^-1 has strong absorption of carboxylic acid ester, 1640c
There was absorption of vinyl group at m ^-1 . This IR spectrum is shown in FIG.

[0034]

Examples I-4 to I-5 Synthesis of [Compound-I] In the same manner as in Example I-2, the catalyst, the silicone compound obtained in Production Example 1 and the allyl methacrylate compound (AMA) were used.
Abbreviated as "), toluene was charged into the reactor, and the reaction temperature was 80 to
The reaction was carried out at 85 ° C.

The results are shown in Table 1.

[0036]

[Table 1]

[0037]

Example II-1 Synthesis of [Copolymer-I] 70 g of toluene was charged into a 300 ml four-necked flask equipped with a thermometer, a stirring rotor, a cooling tube, and a nitrogen supply introducing tube. On the other hand, 36 g of methyl methacrylate, 23 g of n-butyl acrylate, 12 g of 3-methacryloxypropyltrimethoxysilane were added to the dropping funnel, and Example I was used.
29 g of the silicon-based compound obtained in -1 and toluene 3
0 g, azobisisobutyronitrile (AIBN) 1.0
A mixed solution of 2.0 g of g and n-dodecyl mercaptan (LSH) was charged and attached to the 4-necked flask. Nitrogen was supplied into the 4-neck flask, and the inside of the reactor was sufficiently replaced with nitrogen. The mixture was added dropwise while stirring and heating to keep the inside of the 4-neck flask at 80 ° C. After the dropping is completed, the temperature is 80 ° C and the temperature is 5
Stir for hours.

After completion of the reaction, gas chromatographic analysis of the reaction solution revealed that the reaction rate of the (meth) acrylic monomer was 100% methyl methacrylate, 94% n-butyl acrylate, and 99% methacryloxypropyltrimethoxysilane. ..
Analysis results by GPC method MN5800, MW67000
Met. A part of the reaction solution was taken and concentrated under reduced pressure at 60 ° C., and then toluene of the same weight was added to obtain a 50% solution. In the IR analysis of this solution, there was no absorption of a vinyl group at 1640 cm ^-1 . The IR spectrum is shown in FIG.

[0039]

Examples II-2 to II-5 Synthesis of [Copolymer-I] Toluene 20 was placed in a 4-neck flask in the same manner as in Example II-1.
Then, the following mixture was added dropwise at 80 ° C. with a dropping funnel. Then, the mixture was reacted at 80 ° C. for 5 hours. Methyl methacrylate (MMA) 19.9 g n-butyl acrylate (BA) 12.6 g 3-methacryloxypropyltrimethoxysilane 7.0 g Silicone compounds of Examples I-2 to I-5 15.5 g AIBN 0 to _{.55g n-C 12 H 25 SH} 1.10g toluene 35g table 2 shows the results.

[0040]

[Table 2]

[0041]

Examples II-6 to II-9 Synthesis of [Copolymer-I] 70 g of toluene was placed in a 4-neck flask in the same manner as in Example II-1.
Was charged, and the composition liquid of Table 3 was charged into the dropping funnel and reacted in the same manner as in Example II-1. Table 3 shows the charged composition and the result.

[0042]

[Table 3]

[0043]

[Production Example 2] In the same manner as in Example II-1, 70 g of toluene was charged into a 4-necked flask, and the following mixed solution was added dropwise at 80 ° C. with a dropping funnel. Then, the reaction was carried out at a temperature of 80 ° C. for 5 hours. Methyl methacrylate 54 g-n-butyl acrylate 34 g 3-methacryloxypropyltrimethoxysilane 12 g AIBN 1.0 g n-C ₁₂ H ₂₅ SH 2.0 g As a result, the obtained polymer molecular weight (MN) was 5500.

[0044]

Examples III-1 to 9: A curing catalyst (a = aluminum acetyl acetate, b = dibutyltin dilaurate) was added to the resin solutions obtained in Examples II-1 to 8 in an amount of 1% by weight of the resin content. After that, ethyl acetate / xylene (40/60)
The viscosity of the mixed solvent (wt%) was used as a thinner to adjust the viscosity of the paint in a cup # 4 for 15 seconds, and the coating was performed, followed by heat curing at 150 ° C. for 30 minutes to evaluate the performance of the coating film. The results are shown in Table 4.

[0045]

Comparative Example 1 On the other hand, the resin having no side chain of the specific structure of the present invention obtained in Production Example 2 was coated, cured and evaluated in the same manner as in Examples II-1 to 9 to give a comparative example. .. The results are shown in Table 4.
Are also shown.

[0046]

[Table 4]

[0047]

The coating composition thus obtained has a low viscosity and can reduce the amount of diluted organic solvent used, and the obtained cured coating film has excellent gloss and surface smoothness. In addition to providing appearance, it also exhibits excellent weather resistance, acid resistance, alkali resistance, solvent resistance, water repellency, and stain resistance, so for example, new car middle coating and top coating, automobile repair, building exterior, building materials, plastic, various Used as a high-performance paint applicable to various fields such as metal products and woodworking.

[Brief description of drawings]

FIG. 1 is the IR of the compound obtained in Example I-1 of the present invention.
The spectrum is shown.

FIG. 2 is the IR of the compound obtained in Example I-3 of the present invention.
The spectrum is shown.

FIG. 3 is an NM of the compound obtained in Example I-3 of the present invention.
The R spectrum is shown.

FIG. 4 I of the compound obtained in Example II-1 of the present invention
The R spectrum is shown.

Claims (3)

[Claims] 1. A compound having the structures represented by the following general formulas (A) and (B) in the molecular structure (1), and (2) in the case of being bonded to silicon as an end group, R ² —O— and When bonded to oxygen, it has a structure of R ² — (R ² is a linear or branched alkyl group having 1 to 18 carbon atoms, or a phenyl group),
(3) Number average molecular weight of 800 to 200,000, and (4)
A silicone compound having an R ¹ / R ² ratio of 0.8 to 10. [Chemical 1] 2. A compound having the structures represented by the following general formulas (C) and (D) in the molecular structure (1), and (2) in the case of being bonded to silicon as an end group, R ² —O— and When bonded to oxygen, it has a structure of R ² — (R ² is a linear or branched alkyl group having 1 to 18 carbon atoms, or a phenyl group),
(3) A vinyl-based copolymer having a number average molecular weight of 1,000 to 200,000, having a silicone-based functional group having an R ¹ / R ² ratio of 0.8 to 10 in at least one side chain. [Chemical 2] 3. (1) The compound has the structures represented by the following general formulas (C) and (D) in the molecular structure, and (2) in the case of being bonded to silicon as an end group, R ² —O— and When bonded to oxygen, it has a structure of R ² — (R ² is a linear or branched alkyl group having 1 to 18 carbon atoms, or a phenyl group),
(3) Number average molecular weight 1 having a silicone functional group having an R ¹ / R ² ratio of 0.8 to 10 in at least one side chain
A coating composition comprising 000 to 200,000 vinyl-based copolymer as a main component. [Chemical 3]