JP3115928B2 - Silicone compound, vinyl copolymer thereof, and coating composition using the same - Google Patents

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. having excellent 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 terminal or a side chain and a coating composition using the same are disclosed in, for example, JP-A-54-36395 and JP-A-54-40893. JP-A-54-123129
It is publicly known in Japanese Patent Publication No.

[0003]

However, recently,
In the field of construction, the field of automobiles, the field of metal coating, and the like, there is a demand for a coating material having better performance in terms of performance such as weather resistance, acid resistance, solvent resistance, stain resistance, and smoothness.

[0004]

Means for Solving the Problems The present inventors have created a silicone compound having a specific structure having a polymerizable double bond and a copolymer thereof, and applied the above compound to a paint to solve the above-mentioned problems. They have found that they can be solved and have completed the present invention. That is, the present invention (1) has a structure represented by the following general formulas (A) and (B) in the molecular structure,
(2) When R ² —O— is bonded to silicon as a terminal group,
And the case where it binds to oxygen takes the structure of R ² — (R ²
Is a linear or branched alkyl group having 1 to 18 carbon atoms, or a phenyl group), and (3) a number average molecular weight of 800 to 20,000.
0, and (4) a silicone compound [Compound-I], wherein the R ¹ / R ² ratio is 0.8 to 10;

[0005]

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And (1) a compound represented by the following general formula (C)
And (D), and (2) a structure of R ² —O— when bonded to silicon as an end group and a structure of R ² — when bonded to oxygen as a terminal group (where R ² is carbon Numbers 1 to 18
Linear or branched alkyl group or phenyl group),
(3) A vinyl copolymer having a number average molecular weight of 1,000 to 200,000, characterized by having a silicone functional group having an R ¹ / R ² ratio of 0.8 to 10 in at least one side chain. Coupling-I],

[0007]

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And a coating composition comprising the above-mentioned vinyl copolymer as a main component. The above [compound-
The silicone compound represented by the formula (I) is disclosed in, for example,
As described in JP-A-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 a silicon terminal as a terminal group, and R ² — (R
² have the same shows a) a structure supra R ^2, and carbon Si-H groups R ¹ / R ² ratio hydro silicone compound comprising from 0.8 to 10 is [compound -II] having - It is obtained by adding a carbon unsaturated bond compound (hydrosilylation reaction).

[0009]

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As described in the above-mentioned application, this [Compound-II] is hydrolyzed and condensed by reacting water with trichlorosilane or a mixture of trichlorosilane / organotrichlorosilane in a solvent such as dioxane. ,
It is then obtained by reaction with alcohol. The structure of [Compound-II] thus obtained can be represented by the following (G) when a representative example is shown at a relatively low molecular weight, taking the case where R ⁶ is hydrogen and R ² is a methyl group (Me) as an example. , (H) and (Q).

[0011]

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[0012]

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[0013]

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Examples of the carbon-carbon unsaturated bond compound to be added to [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 acetate, allyl esters such as allyl propionate, allyl 2-ethylhexanoate, 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 and ethyl vinyl ether And 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 esters.

Of these, terminal olefins such as 1-hexene and 1-octene, allyl esters and allyl ethers are preferred from the viewpoint of reactivity. 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 bonds such as allyl glycidyl ether and glycidyl (meth) acrylate. And an epoxy compound in one molecule. Of these, allyl glycidyl ether is preferably used. Examples of the carbon-carbon unsaturated bond compound for introducing a polymerizable double bond into the silicone compound represented by [Compound-I] include, for example, allyl (meth) acrylate,
Two or more double bond groups such as diallyl ether, diallyl phthalate (meth) vinyl acrylate, vinyl crotonate, vinyl cinnamate, ethylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, etc. Compounds which are combined in one molecule may be mentioned. Of these, particularly preferred is allyl (meth) acrylate.

In the reaction of [Compound-II] with the unsaturated bond compound of the present invention, it is preferable to use a platinum group VIII catalyst. Examples of the group VIII platinum-based catalyst include platinum alone, chloroplatinic acid, alcohol-modified chloroplatinic acid, platinum chloride-olefin complex, alumina and silica, etc. on which solid platinum is supported, 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 relative to the reactants.
An amount of 0 ppm is used.

The hydrosilylation reaction is carried out at 50 to 150
At a temperature of ° C., a reaction time of 1-5 hours is achieved. When the reaction temperature is 50 ° C. or lower, the reaction rate becomes slow, which is not practical. On the other hand, when the reaction temperature is 150 ° C. or higher, a high molecular weight product is partially generated or a gelation 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. The binding compound is preferably in the range of 0.1 to 50 mol.

In this reaction, a solvent may be used.
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 and xylene is used. When a solvent is used, it is preferable to use 0.1 to 10 parts by weight based on 1 part by weight of the raw material used for the reaction.

The silicone compound [compound-I] thus obtained has a cyclic silicone structure and / or a ladder-type silicone structure and a hydrolyzable alkoxysilyl group in the molecule, and It has a polymerizable double bond or 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.

This compound having a polymerizable double bond [compound-
I] is another polymerizable vinyl monomer copolymerizable therewith.
To form a vinyl copolymer [Copolymer-I] having a residue of [Compound-I] in the side chain. As the vinyl monomers to be copolymerized, it is possible to use, for example, the carbon-carbon unsaturated bond compounds 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 esters such as (meth) acrylic acid-3- (triethoxysilyl) propyl and isobornyl (meth) acrylate, (meth) acrylic acid, styrene and the like are preferably used.

At the time of 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 as usual. As the solvent, aromatic hydrocarbons such as benzene, toluene, and xylene, esters such as ethyl acetate, butyl acetate, and 2-ethylhexyl acetate, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone are generally 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 ordinary temperature to about 150 ° C. The molecular weight of the obtained copolymer can be controlled by the type and amount 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, if necessary, an epoxy group. Heat curing, moisture curing, catalyst curing, etc. are possible, and raw materials for coatings, raw materials for coating agents,
It is a novel copolymer useful as a raw material for a ring agent and a raw material for an adhesive.

When a resin having a specific structure obtained by the present invention is applied to a coating material, the resin is diluted with an aprotic solvent as required and applied and cured. In curing, it is preferable to use an accelerating catalyst. Typical examples of such curing catalysts include monomethyltin triacetate, dimethyltin diacetate, dibutyltin diacetate, dibutyltin di-2-ethylhexanoate, dibutyltin dilaurate, and diphenyltin. Dioctate, bis (dibutyltin monolaurate)
Tin compounds such as sulfide, monobutyltin dilaurate hydrochloride, tin 2-ethylhexanoate, dibutyltin oxide, zinc hexanoate, zinc 2-ethylhexanoate, zinc acetylacetonate, bis (zinc monoacetoacetate) )
Oxides, bis (zinc monoacetate) oxide, zinc compounds such as zinc dibenzoylmethane, lead compounds such as lead hexanoate, lead 2-ethylhexanoate, lead acetylacetonate, diisopropoxy bis ( Ethyl acetoacetate
G) titanium chelate compounds such as titanate, diisopropoxy bis (acetylacetate) titanate or diisopropoxy bis (acetylacetone) titanate; diisopropylate ethyl acetoacetate aluminum; Tris (ethyl acetate) aluminum, tris (n-propyl acetoacetate) aluminum,
Aluminum tris (isopropylacetoacetate), aluminum tris (n-butylacetoacetate), aluminum tris (acetylacetonate), aluminum tris (ethylacetonate), aluminum diisopropylateethylacetonate, monoacetylacetate Nabis bis (ethylacetonate) aluminum, monoethylacetoacetate bis (acetylacetonate) aluminum, tris (isopropylate)
Aluminum chelate compounds such as aluminum, tris (sec-butylate) aluminum, diisopropylatemono-sec-butoxyaluminum or trisacetylacetonealuminum, tetrakis (acetylacetone) zirconium, tetrakis (n-propylacetoacetate) zirconium A zirconium compound such as tetrakis (acetylacetonate) zirconium or tetrakis (ethylacetoacetate) zirconium, triethylamine, tributylamine, N, N,
N ', N'-trimethylethylenediamine, ethylenediamine, diethylenetriamine, diazabicyclooctane, polyamide polyamine of dimer acid, isophoronediamine, xylylenediamine, diaminodiphenylmethane, phthalic anhydride, tetrahydrophthalic anhydride, pyromellitic anhydride, anhydride And epoxy curing agents such as trimellitic acid, phenol novolak, polymercaptan, polysulfide, and 2-methyl-4-ethylimidazole.

These catalysts may be used as a mixture as appropriate. The amount of the catalyst is usually 0.005% to 5% based on the resin.
It is selected from the range of weight%. The curing temperature depends on the properties of the substrate,
Although it can be set freely according to the purpose of coating, it can be generally selected from a range from natural drying at atmospheric temperature to baking hardening at about 220 ° C. At the time of coating, additives such as an antioxidant, a light stabilizer and a viscosity controlling agent, pigments for coloring, metal powder such as aluminum paste, and the like can be added as required.

[0026]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which by no means limit the present invention. The NMR analysis in the examples was performed by PMX
As for 60Si and infrared absorption spectrum (IR), JASCO Corporation FT / IR-5300 was used. The molecular weight is measured by gel permeation chromatography (GPC).
In Production Example 1, Toso-TSK gel G5000HXL + G2500HXL, and in Examples, Shodex KF-805 + KF-804 + K
An F-802 column system was used.

The coating film performance was evaluated according to the following method. 1) Mitsuzawa: JIS K5400-7.6 (60
°) ○: Specular gloss = 85% or more 2) Surface smoothness: Surface roughness profile measuring device “Surfcom-5”
54AD "(manufactured by Tokyo Seimitsu Co., Ltd.) Surface properties (good) ○>△> × (poor) 3) Gel fraction: The cured coating film was immersed in acetone, and heated at 20 ° C.
4) Pencil hardness: JIS K5400-8.4.1 (evaluation of scratches) 5) Adhesion: JIS K5400-8.5.2.
○: 10 to 8 points, Δ: 6 to 4 points, ×: 2 to 0 points 6) Flexibility: JIS K5400-8.1 ○:
2mmφ passed, Δ: 3-6mmφ passed ×: 8mmφ
7) Stain resistance: JIS K5400-8.10.
：: no change, Δ: slight change, ×: remarkable change 8) Acid resistance: JIS K5400-8.22 9) Alkali resistance: JIS K5400-8.21 (5)
10) Solvent resistance: JIS K5400-8.24 (toluene) 11) Weather resistance: ASTM G-53 ○: 2500
Gloss retention rate after exposure to time = 95% or more ×: Gloss retention rate after exposure for 2500 hours = 90% or less

[0028]

Production Example 1 Synthesis of [Compound-II] 1200 g of dioxane and 1 mol of trichlorosilane were charged into a 2-liter four-necked flask equipped with a thermometer, a stirring rotor and a cooling tube, and stirred. 18 g of water and dioxane 1
A dropping funnel containing 8 g was attached to the above four-necked flask,
The solution was added dropwise while maintaining the temperature at 25 to 30 ° C. After dropping, 3 more
After stirring was continued for 0 minutes, a dropping funnel containing 3 mol of ethanol was attached, and the mixture was added dropwise at 25 to 30 ° C.
Thereafter, the mixture was further stirred for 120 minutes. Take out the reaction solution,
When the solvent was completely distilled off under reduced pressure at about 60 ° C. or less, 7
9.3 g of a low viscosity silicone compound was obtained. This liquid was dissolved in chloroform, and this solution was gel-permeated.
The molecular weight was measured by traction chromatography (hereinafter abbreviated as GPC method). As a result, the number average molecular weight (hereinafter abbreviated as MN) 840 and the weight average molecular weight (hereinafter MW)
1600). ^{According to 1} H-NMR, Si-
H / OC ₂ H ₅ was about 1.2. Also, this silico
The compound was added to 2N-NaOH, and the content of Si-H was measured by the generated hydrogen gas.
mmol / g of hydrogen gas was generated.

[0029]

Example I-1 Synthesis of [Compound-I] Isopropano containing 8% chloroplatinic acid was placed in a 200 ml four-necked flask equipped with a thermometer, a stirring rotor, a cooling tube, and an inlet tube for supplying nitrogen. Then, 0.32 g of a toluene solution, 3.41 g of allyl methacrylate, 27.69 g of allyl glycidyl ether and 50.8 g of toluene were charged. In addition, the silicone compound obtained in Production Example 1 was dropped onto a dropping funnel.
9 g was charged and attached to the 4-neck flask. A small amount (approximately 5 ml / min) of nitrogen was flowed, stirred, and heated to increase the temperature. When the temperature inside the flask rises to 70 ° C.,
The dropping of the compound was started, and the whole amount was dropped while maintaining the temperature at 80 to 85 ° C. After completion of the dropwise addition, the mixture was stirred at a temperature of 80 to 85 ° C for 3 hours. After completion of the reaction, the reaction solution was subjected to gas chromatography.
Analysis showed that the conversion of allyl methacrylate was 70.
% And the conversion 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. The molecular weight of this liquid was measured by the GPC method.
900. When this liquid was added to 2N-NaOH and the residual Si-H was measured, the reaction rate of Si-H was 76%. In the IR analysis (infrared absorption spectrum), the absorption of a carboxylic acid ester was at 1720 cm ^-1 and the absorption of a vinyl group was at 1640 cm ^-1 . FIG. 1 shows the IR spectrum.

[0031]

Example I-2 Synthesis of [Compound-I] A 200 ml four-necked flask equipped with a thermometer, a stirring rotor, a cooling tube, and a nitrogen supply inlet tube was sufficiently replaced with nitrogen to obtain platinum black. 0.5 g, and then Production Example 1
19.2 g of silicone compound of formula (1), 1-hexene 16.9
g, allyl methacrylate 4.85 g, toluene 40.9
g of the mixture was added. Start stirring and heating, 80 ~ 8
The temperature was raised to 5 ° C. The mixture 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 at about 60 ° C.
g of recovery was obtained. According to gas chromatography of the reaction solution, the conversion of 1-hexene was 57%, the conversion of allyl methacrylate was 90%, and the conversion of Si-H was 73%.
N was 1700.

[0032]

Example I-3 Synthesis of [Compound-I] In the same apparatus as in Example I-1, 0.10 g of an isopropanol solution containing 8% chloroplatinic acid, and 7.5 allyl acetate were used.
g, 8.3 g of the silicone compound obtained in Production Example 1, and 15.8 g of xylene, and the mixture was stirred at a temperature of 80 to 85 ° C. for 2 hours. Thereafter, 6.3 g of allyl methacrylate was added dropwise and reacted at 80 to 85 ° C. for 2 hours. Approximately 45
When the solvent was distilled off under reduced pressure at 15.degree. C., 15.2 g of a recovered product was obtained. As a result of gas chromatography analysis of the reaction solution, the conversion of allyl acetate was 95%, and the conversion of allyl methacrylate was 19%. The molecular weight was measured by the GPC method.
It was 0. The conversion of Si-H was 85%.

¹ H-NMR analysis results: 5.4 to 6.4 p
pm, CH ₂ ＣC = group is 0.5-1.1 ppm, and Si—
It can be seen that there is a CH ₂ — group. The ¹ H-NMR spectrum is shown in FIG. As a result of IR analysis, 1750 cm ⁻¹
Has strong absorption of carboxylic acid ester, 1640cm
^-1 had vinyl group absorption. 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, the allyl methacrylate compound (AMA)
), Toluene was charged into the reactor, and the reaction temperature was 80 to
The reaction was performed at 85 ° C.

Table 1 shows the results.

[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 an inlet tube for supplying nitrogen. 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.
29 g of the silicone-based compound obtained in -1 and toluene 3
0 g, azobisisobutyronitrile (AIBN) 1.0
g and n-dodecyl mercaptan (LSH) (2.0 g), and the mixture was placed in the four-necked flask. Nitrogen was supplied into the four-necked flask, and the inside of the reactor was sufficiently replaced with nitrogen. The mixture was stirred and heated, and the mixture was dropped while maintaining the inside of the four-necked flask at 80 ° C. After the completion of dropping, 5
Stirred for hours.

After completion of the reaction, the reaction mixture was analyzed by gas chromatography. As a result, the conversion of the (meth) acrylic monomer was 100% for methyl methacrylate, 94% for n-butyl acrylate, and 99% for methacryloxypropyltrimethoxysilane. .
Analysis result by GPC method MN5800, MW67000
Met. A part of the reaction solution was taken, concentrated at 60 ° C. under reduced pressure, and the same weight of toluene 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 . FIG. 4 shows the IR spectrum.

[0039]

Examples II-2 to II-5 Synthesis of [Copolymer-I] As in Example II-1, toluene 20 was added to a four-necked flask.
g, and the following mixture was added dropwise at 80 ° C. with a dropping funnel. Thereafter, the reaction was carried out at 80 ° C. for 5 hours. Methyl methacrylate (MMA) 19.9 g n-butyl acrylate (BA) 12.6 g 3-methacryloxypropyltrimethoxysilane 7.0 g Silicon-based compounds of Examples I-2 to I-5 15.5 g AIBN 0 .55 g nC ₁₂ H ₂₅ SH 1.10 g Toluene 35 g Table 2 shows the results.

[0040]

[Table 2]

[0041]

Examples II-6 to II-9 Synthesis of [Copolymer-I] 70 g of toluene in a four-necked flask in the same manner as in Example II-1.
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 compositions and the results.

[0042]

[Table 3]

[0043]

Production Example 2 In the same manner as in Example II-1, 70 g of toluene was charged into a four-necked flask, and the following mixture was dropped at 80 ° C. through a dropping funnel. Thereafter, 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 polymer molecular weight (MN) obtained was 5,500.

[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 1-8 by 1% by weight of resin. After that, ethyl acetate / xylene (40/60)
(Wt%) of the mixed solvent was used as a thinner and the viscosity was adjusted for 15 seconds with a hood cup # 4 for 15 seconds, and the coating was heated and cured at 150 ° C. for 30 minutes to evaluate the performance of the coating film obtained. Table 4 shows the results.

[0045]

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

[0046]

[Table 4]

[0047]

As described above, the coating composition thus obtained has a low viscosity and the amount of the diluting organic solvent used can be reduced, and the resulting cured coating film has excellent gloss and surface smoothness. In addition to providing the appearance, it also has excellent weather resistance, acid resistance, alkali resistance, solvent resistance, water repellency, and stain resistance.For example, new car middle coat and top coat, car repair, building exterior, building materials, plastics, various types It is used as a high-performance paint applicable to various fields such as metal products and woodwork.

[Brief description of the drawings]

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

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

FIG. 3 shows the NM of the compound obtained in Example I-3 of the present invention.
2 shows an R spectrum.

FIG. 4 shows I of the compound obtained in Example II-1 of the present invention.
2 shows an R spectrum.

Claims (3)

(57) [Claims] (1) The molecular structure has both structures represented by the following general formulas (A) and (B), and (2) 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 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. Embedded image (2) R ² —O— and (2) having a structure represented by the following general formulas (C) and (D) in the molecular structure, and (2) bonding to silicon as a terminal group. 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) R ¹ / R ² ratio number average molecular weight 1,000 to 200,000 vinyl copolymer, characterized by having in at least one side chain of the silicone-based functional groups is 0.8 to 10. Embedded image 3. A compound having (1) a structure represented by the following general formulas (C) and (D) in its molecular structure, and (2) 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 at least one silicone-based functional group having an R ¹ / R ² ratio of 0.8 to 10 in at least one side chain.
A coating composition comprising, as a main component, a vinyl copolymer of 000 to 200,000. Embedded image