JPH10101987A - Acrylic silicone emulsion composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coating acrylic silicone emulsion composition highly safe and excellent in film performances such as weathering, staining and water resistances. SOLUTION: This composition comprises 20-99wt.% acrylic resin emulsion (A) prepared by emulsion-polymerizing a monomer mixture comprising 60-97wt.% (meth)acrylic ester monomer, 1-10wt.% α,β-unsaturated carboxylic acid, 1-10wt.% polymerizable emulsifier and 1-20wt.% polymerizable light stabilizer, 0-30wt.% organoalkoxysilane compound (B) having at least one glycidyl group in the molecule and 1-50wt.% polymerizable silicone compound (C).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an emulsion composition for paints used for painting building materials and the like, and more particularly to an acrylic silicone emulsion composition for paints having excellent weather resistance and chemical resistance.

[0002]

2. Description of the Related Art In the coating and painting of architectural and building materials, not only does the base of concrete, mortar, wood, etc. be protected, but also the design appearance and beautiful decorative appearance formed by painting do not change over a long period of time. It is desired to be continued, and from such a viewpoint, acrylic silicone resin paint, fluororesin paint and the like are preferably used.
However, these are paints based on organic solvents, which are not desirable from the viewpoint of environmental protection and energy saving.

[0003] Therefore, as a safe and environmentally friendly paint,
Although water-based emulsion paints such as acrylic resin emulsion paints were developed, water resistance, alkali resistance,
Excellent basic properties required for paints such as weather resistance have not been found in a well-balanced manner.

For this reason, in order to improve these various properties, an acrylic silicone emulsion obtained by converting an acrylic resin emulsion into a silicone has been proposed.
At the stage of preparing the acrylic resin, for example, a radically polymerizable silane compound such as γ-methacryloyloxypropyltrimethoxysilane is used, and the compound is siliconeized by copolymerization. It undergoes hydrolysis and crosslinks within the emulsion particles. As a result, not only storage stability is deteriorated and film forming property is deteriorated, but also at the time of forming a coating film, sufficient fusion (coalescence) and cross-linking between emulsion particles do not progress, and The leveling property at the time of film formation was reduced, making it difficult to obtain gloss, and the expected weather resistance was not obtained.

[0005] On the other hand, when a method of suppressing the crosslinking of the alkoxysilane during polymerization or during storage, for example, copolymerization of an amide compound or an amino compound is used, the crosslinking is not affected even during the formation of a coating film. This was greatly suppressed, and satisfactory coating film performance was not finally obtained.

[0006] As means for silicone conversion, copolymerization of silicone macromonomer has been proposed (PA
INT & COATING BUSINESS Vol.
6, 1996), the silicone polymer segment did not crosslink, and when applied to building materials, the blocking properties were poor due to the silicone polymer segment. In addition, touch-up is required in building material coating, but the recoating property is poor, which is not preferable.

[0007]

SUMMARY OF THE INVENTION The present invention solves the above-mentioned drawbacks of the prior art and is a highly safe acrylic silicone emulsion having excellent coating performance not inferior to the conventional acrylic silicone resin paint. It is intended to provide a resin for use.

[0008]

To achieve the above object, the present invention has the following arrangement.

That is, (meth) acrylic acid ester monomer (1) 60 to 97% by weight, α, β-unsaturated carboxylic acid (2) 1 to 10% by weight, polymerizable emulsifier (3) 1 to 10%
% Of an acrylic resin emulsion (A) obtained by emulsion polymerization of a monomer mixture comprising 1 to 20% by weight of a polymerizable light stabilizer (4), and at least one acrylic resin emulsion per molecule. An acrylic silicone emulsion composition comprising 0 to 30% by weight of an organoalkoxysilane compound having a glycidyl group (B) and 1 to 50% by weight of a polymerizable silicone compound (C).

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS (Meth) acrylic acid ester monomer (1) includes methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, tertiary butyl acrylate, cyclohexyl acrylate,
2-ethylhexyl acrylate, lauryl acrylate,
Tricyclodecyl acrylate, isobornyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate, stearyl methacrylate, Examples thereof include tridecyl methacrylate and isobornyl methacrylate, and these monomers may be used alone or in a mixture of two or more. In particular, when the content of isobornyl methacrylate in the (meth) acrylic acid ester monomer is 5% by weight or more, the coating film performance when the acrylic silicone emulsion compound of the present invention is used in a coating material is further improved. It is preferred in that respect.

The (meth) acrylate monomer (1) is used in an amount of 60 to 97% by weight when the acrylic resin emulsion (A) is emulsion-polymerized. 60% by weight
When the amount is less than the above, basic performance as a coating film such as adhesion, elongation, gloss, and chemical resistance in the case of a paint cannot be obtained. Strength becomes insufficient.

Examples of the α, β-unsaturated carboxylic acid (2) include acrylic acid, methacrylic acid, maleic acid and itaconic acid.
It may be used as a mixture of two or more.

The above-mentioned α, β-unsaturated carboxylic acid (2)
Is used in an amount of 1 to 10% by weight when the acrylic resin emulsion (A) is emulsion-polymerized. If the amount is less than 1% by weight, the acrylic resin cannot be sufficiently converted into a silicone, and the coating film obtained when used as a coating composition is unsatisfactory in hardness, scratch resistance, weather resistance, and the like. If it exceeds 10% by weight, the water resistance of the coating film,
The chemical resistance deteriorates and the emulsion viscosity increases.

Examples of the polymerizable emulsifier (3) include polyethylene glycol monoacrylate and polyethylene glycol monomethacrylate having various molecular weights (different EO addition moles), polyoxyethylene alkylphenyl ether acrylate, polyoxyethylene alkylphenyl. Ether methacrylate, ammonium 2-acryloyloxyethylsulfonate, sodium 2-methacryloyloxyethylsulfonate, monomaleic acid esters of polyoxyethylene glycol and derivatives thereof, polyoxyalkylene alkyl ether phosphate esters, and the like, These emulsifiers may be used alone or as a mixture of two or more.

In particular, when the polymerizable emulsifier has an acrylic or allylic functional group and is represented by Formula I or Formula II, coagulum during the preparation of the acrylic resin emulsion (A) decreases, It is preferable because a more stable acrylic resin emulsion can be obtained and aggregation and gelation in preparing the acrylic silicone emulsion composition can be further prevented.

[0016]

Embedded image

Embedded image The polymerizable emulsifier represented by the formula I is generally referred to as bis (polyoxyethylene polycyclic phenyl ether) (meth) acrylated sulfate ester salt, and these may be appropriately selected.

The polymerizable emulsifier represented by the formula II includes:
In the formula, X is H or SO ₃ NH ₄ , but in the present invention, SO ₃ NH ₄ is preferable.

The polymerizable emulsifier (3) is used in an amount of 1 to 10% by weight when the acrylic resin emulsion (A) is emulsion-polymerized. When the amount is less than 1% by weight, coagulum increases during emulsion polymerization, and coagulation,
Causes gelation. If the content exceeds 10% by weight, the basic properties such as water resistance and alkali resistance of the coating film when it is used as a coating material are deteriorated.

As the polymerizable light stabilizer (4), 2,4-
Dihydroxybenzophenone, 2-hydroxy-4
-(3-methacryloxy-2-hydroxypropoxy) benzophenone, 2-hydroxy-4- (3-
Acryloxy-2-hydroxypropoxy) benzophenone, 2,2'-dihydroxy-4- (3-methacryloxy) -2-hydroxypropoxy) benzophenone, 2,2'-dihydroxy-4- (3-acryloxy -2-hydroxypropoxy) benzophenone and the like, and these polymerizable light stabilizers alone,
Alternatively, they can be used as a mixture of two or more.

In the present invention, in particular, the polymerizable light stabilizer is represented by the formula I
When represented by II, the storage stability of the acrylic resin emulsion (A) and the long-term light stability effect are excellent,
In addition, the acrylic resin emulsion (A) is emulsion-polymerized,
During preparation, the occurrence of coagulum is minimized,
Moreover, it is preferable in that the acrylic resin emulsion (A) can be obtained without agglomeration or gelation.

[0021]

Embedded image Examples of the polymerizable light stabilizer represented by the formula III include 2- (2
'-Hydroxy-5'-acryloyloxyethylphenyl) -2H-benzotriazole, 2- (2'-hydroxy-5'-methacryloyloxyethylphenyl)
-H-benzotriazole.

The polymerizable light stabilizer (4) is used in an amount of 1 to 20% by weight when the acrylic resin emulsion (A) is emulsion-polymerized.
used. If the amount is less than 1% by weight, sufficient weather resistance of the coating film as a coating cannot be obtained. If the content exceeds 20% by weight, the storage stability of the acrylic resin emulsion or acrylic silicone emulsion composition deteriorates, which is not preferable.

The acrylic resin emulsion (A) is prepared, for example, in ion-exchanged water at a polymerization temperature of 30 to 100 ° C., and as a polymerization initiator, ammonium persulfate, potassium persulfate, tertiary butyl hydroperoxide, α, α'-azobisisopropane. Using butyronitrile, tertiary butyl-peroxy-2-ethylhexanoate, etc., the above-mentioned (meth) acrylate monomer, α, β-unsaturated carboxylic acid, polymerizable emulsifier, polymerizable It is prepared by emulsion polymerization of a mixture of light stabilizers.

At this time, the weight average molecular weight of the acrylic resin emulsion (A) is preferably 100,000 or more in view of chemical resistance and coating film strength (toughness (strength, elongation) of the coating film). The particle size of the dispersed polymer particles is 50 to 3
It is preferably 00 nm in terms of paint viscosity, film-forming properties, uniformity of the coating film, and drying property, and the weight average particle diameter / number average particle diameter is 3 or less, more preferably 2 or less, for preventing aggregation. It is preferred in that respect.

In the acrylic silicone emulsion composition of the present invention, the amount of the acrylic resin emulsion (A) needs to be 20 to 99% by weight. If the amount is less than 20% by weight, the elongation of the coating film as a coating material is reduced, and the coating film is liable to crack and peel off. If the content exceeds 99% by weight, the degree of silicone conversion becomes too low, the hardness of the coating film decreases, and the scratch resistance and stain resistance deteriorate.

Further, an organoalkoxysilane compound (B) having at least one glycidyl group in one molecule
Are γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ
-Glycidoxypropyltriisopropyloxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3,4 epoxycyclohexyl) ethyltrimethoxysilane, and the like.
Alternatively, a mixture of two or more types may be used. Also,
(Partial) condensates of these compounds may be used.

In the acrylic silicone emulsion composition of the present invention, the amount of the organoalkoxysilane compound (B) having at least one glycidyl group in one molecule must be 0 to 30% by weight. If it exceeds 30% by weight, the coating film becomes too brittle, and cracks and peeling are likely to occur. Further, the storage stability of the acrylic silicone emulsion composition deteriorates.

Further, as the polymerizable silicone compound (C), γ-methacryloyloxypropyltrimethoxysilane, γ-methacryloyloxypropyltriethoxysilane, γ- (2-aminoethyl) aminopropyltrimethoxysilane, γ- ( 2-aminoethyl) aminopropyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, vinyltriacetoxysilane, γ
-Chloropropyltrimethoxysilane, vinyltrimethoxysilane, dimethyldimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, hydroxypropyltrimethoxysilane, ureidopropyltrimethoxysilane, γ-ureidopropyltrimethoxysilane, γ
-Ureidopropyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltriisopropyl Examples include oxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3,4 epoxycyclohexyl) ethyltrimethoxysilane, and condensates of these compounds.
It may be a mixture of more than one kind. Further, a condensate of these compounds or a mixture of a condensate and a monomer may be used.

The acrylic silicone emulsion composition of the present invention contains 1 to 50% by weight of the above-mentioned polymerizable silicone compound (C), so that an organoalkoxy having at least one glycidyl group in one molecule can be obtained. Dramatically improves the storage stability of the acrylic resin emulsion siliconeized with the silane compound (B), lowers the film-forming temperature, enables film formation with the addition of a small amount of a film-forming auxiliary, and improves the film performance. , And the cross-linking property of the polymer at the time of forming a coating film is improved.

In the present invention, when the polymerizable silicone compound (C) is a mixture of dimethoxymethylphenylsilane, trimethoxyphenylsilane, and a silicone compound having a reactive functional group at a terminal or a side chain, the effect of the present invention is obtained. Is more remarkable.

At this time, if the weight ratio of the volatile component / nonvolatile component of the polymerizable silicone compound is 99/1 to 70/30, the polymerizable silicone compound (C) is added to the acrylic resin emulsion (A) and blended. This is preferable in terms of separation and aggregation of the acrylic silicone emulsion composition and storage stability of the acrylic silicone emulsion composition.

Further, a silicone compound having a reactive functional group at a terminal or a side chain is represented by the formula IV or V, wherein the functional group is hydroxyl, epoxy, amino, methoxy, ethoxy, n-propyloxy. Group, a compound having one or more selected from i-propyloxy groups, the acrylic silicone emulsion composition has further improved storage stability, cross-linkability when used as a paint, and various properties such as weather resistance. It is preferable in terms of improvement.

[0033]

Embedded image

Embedded image For the polymerizable silicone compound, for example, a mixed solution of dimethoxymethylphenylsilane and trimethoxyphenylsilane is first prepared as a volatile component, and then, while stirring, the compound corresponding to the formula IV or V of the non-volatile component is gradually added and dissolved. It is produced by doing. At this time, alcohols such as methyl alcohol, ethyl alcohol, and isopropyl alcohol, trimethyl orthoacetate, triethyl orthoacetate, trimethyl orthoformate, triethyl orthoformate, and the like in terms of suppressing undesired reactions, condensation, and gelation during production. It is effective to add a water reducing agent.

In the acrylic silicone emulsion composition of the present invention, the polymerizable silicone compound (C) comprises 1
５０50% by weight. If less than 1% by weight,
The storage stability of the acrylic silicone emulsion composition is insufficient, and gelation may occur during storage. 5
When the amount exceeds 0% by weight, the solvent resistance of the coating film when it is used as a coating material is deteriorated, and the coating film becomes soft and the scratch resistance and the blocking resistance are deteriorated.

The acrylic silicone emulsion composition is prepared by, for example, preparing an acrylic resin emulsion (A) by using an organic or inorganic basic compound such as ammonia, triethylamine, dimethylaminoethanol or the like and having a ^pH (at 25 ° C.) of 7%.
After neutralization to 11, the organoalkoxysilane compound (B) having at least one glycidyl group in one molecule is added and mixed with gentle stirring. After the addition is completed, the polymerizable silicone compound (C) is added and mixed. After completion of the addition of the polymerizable silicone compound (C), it is prepared by allowing to stand at room temperature (the temperature is not particularly limited) for about 10 hours.

Hereinafter, the present invention will be described in more detail with reference to Examples. In addition, each evaluation in an Example shall measure and judge by the following methods. 1. Storage stability Acrylic silicone emulsion composition of about 80 g is put in a 100 ml glass bottle, sealed and sealed at 23 ° C and 40 ° C.
For one month. One month later, the flow state was visually determined. ○ Good without agglomeration and thickening ... Pass △ Generates agglomerates ・ ・ ・ Fail × Gelation ・ ・ ・ Fail

2. Film forming properties (ASTM-D2354-65)
T-12) Acrylic silicone emulsion composition with CS-12
(Film-forming aid manufactured by Chisso Corporation) was added in an amount of 5 phr, and the film-forming temperature was measured. Film forming temperature (M
FT) The film forming temperature was measured in the range of 0 to 50 ° C. using a test apparatus. ○ Shows the film forming temperature as designed and is good ・ ・ ・ Pass △ Shows film forming temperature 10-15 ° C or more higher than the design value ・ ・ ・ Fail × Cannot measure film forming temperature in this test range ・ ・·failure

3. Weather resistance (according to JIS K 5400) Spray paint on JIS A 5413 asbestos cement pearlite board so that the coating thickness is around 50 μm.
Dried at 3 ° C. for 2 weeks. Using the coated plate after drying, using a sunshine weather-O-meter (SWOM), 2
The accelerated weathering test was performed for 000 hours. 8 gloss retention
0% or more is regarded as a pass level.

4. Stain resistance Paint is applied to a glass plate with a 10 mil applicator,
Dried at 23 ° C. for 2 weeks. Approximately 1 g of carbon black was sprayed on the coated plate, gently wiped off with a brush, and the degree of contamination with carbon black was visually determined. ○ After wiping with a brush, it returned to the state before contamination and was good ... Pass △ Slight black brush marks remained ... Pass × The more it was wiped with a brush, the darker it was and the poorer the contamination ... Pass

5. Gel fraction The paint was applied to a polypropylene plate with a 10 mil applicator and dried at 23 ° C for 2 weeks. This coating film was peeled off from the polypropylene plate, and the amount of unextracted acetone was determined with a Soxhlet extractor using acetone as a solvent. The ratio of the weight of the unextracted acetone to the weight of the coating film before Soxhlet extraction was defined as the gel fraction. The higher the gel fraction, the more the crosslinking progresses, and the better the crosslinkability. Gel fraction 80
% Or more is regarded as a pass level.

6. Apply the water-resistant paint on a glass plate with a 10 mil applicator,
Immediately after the application, it was transferred to a container whose temperature was controlled at 5 ° C.
After drying at 5 ° C. for 3 hours, the film was immersed in ion-exchanged water at 23 ° C. for 5 hours, and changes in the appearance of the coating film were visually observed. ○ The appearance of the coating film before and after the water resistance test is good with no difference ・ ・ ・ Pass △ The coating film is slightly whitened, but returns to the original state after moisture drying ・ ・ ・ Pass × The coating film flows. Whitening and blistering ・ ・ ・ Fail

[0042]

EXAMPLES In the following Examples and Comparative Examples, Tables 1 to 5
Of each of the raw materials (1) to (4) (g) of the weight shown in each table. In the table, AN-MS-60: Polymerizable emulsifier (Nippon Emulsifier Co., Ltd.)
SE-10N: polymerizable emulsifier (manufactured by Asahi Denka Co., Ltd.), formula I
DBS (sodium dodecylbenzenesulfonate): non-polymerizable emulsifier RUVA-93: polymerizable light stabilizer (Otsuka Chemical Co., Ltd.)
SH-6018: polymerizable silicone compound (manufactured by Toray Dow Corning Silicone Co., Ltd.), equivalent to formula V PS-340: polymerizable silicone compound (Chisso Corporation)
MTS: γ-methacryloyloxypropyltrimethoxysilane, QP8-5314: means a polymerizable silicone compound (manufactured by Toray Dow Corning Silicone Co., Ltd.). Represents the sum of the active ingredients.

Example 1 A 2 L four-necked flask equipped with a stirrer, a thermometer, a condenser, and a monomer supply pump was charged with 417.
Charge 2 g. Separately, ion-exchanged water 198.8
g, ammonium persulfate 2.0 g, Example 1 of Tables 1-3
Is emulsified at 5000 rpm for 10 minutes using a homogenizer (Maximum homogenizer manufactured by Nippon Seiki Co., Ltd.). (This is referred to as monomer EM) 10% by weight of the monomer EM is charged into the flask, and the temperature is raised to 80 ° C. in 30 minutes while stirring. 30 more
The polymerization is continued for a minute and then the remaining 90% by weight of the monomer EM is fed into the flask in 3 hours. After further polymerization at 80 ° C. for 1 hour, the mixture is cooled to 40 ° C. A mixture of 9.9 g of ion-exchanged water and the raw material shown in Table 3 as a neutralizing agent is added little by little into the flask to obtain a neutralized acrylic resin emulsion. The weight average molecular weight of this acrylic resin emulsion was 200,000 or more as measured by GPC, and the pH was 9.0.
Met. Particle size (LPA-3000 manufactured by Otsuka Chemical Co., Ltd.)
Measured at 25 ° C.) was 85 nm, which is almost a monodispersion of dw / dn = 1.2. While continuously stirring this neutralized acrylic resin emulsion in the flask,
Was gradually added, and the mixture was further stirred for 1 hour. Furthermore, the raw materials which were previously stirred and mixed to form a uniform solution were gradually added, and further stirred for 1 hour to obtain an acrylic silicone emulsion composition. Table 6 shows the results of examining the storage stability and film forming properties of the obtained acrylic silicone emulsion composition. The obtained acrylic silicone emulsion composition was blended with 10 phr of CS-12 (a film-forming aid manufactured by Chisso Corporation) to prepare a paint for a test, and weather resistance, stain resistance, gel fraction, and water resistance were measured. Table 6 shows the results of the examination. As is clear from Table 6, sufficiently satisfactory results were obtained in all respects.

Examples 2 to 12 The acrylic silicone emulsion compositions of Examples 2 to 12 were prepared in the same manner as in Example 1 except that the raw materials and the amounts used were changed as shown in Tables 1 to 5. Example 1
Table 6 shows the results obtained by examining the respective properties when the composition and the paint were used in the same manner as in the above. As is clear from Table 6, sufficiently satisfactory results were obtained in all respects. The weight-average molecular weight, ^pH , particle size distribution, and particle size of the neutralized acrylic resin emulsion of each example were as shown in Table 7.

Comparative Examples 1 to 5 Acrylic silicone emulsion compositions of Comparative Examples 1 to 5 were prepared in the same manner as in Example 1 except that the raw materials and the amounts used were changed as shown in Tables 1 to 5. Table 6 shows the results obtained by examining the respective properties when the composition and the paint were used in the same manner as in Example 1. As is clear from Table 6, no practically satisfactory product was obtained. The weight-average molecular weight, ^pH and particle size of the neutralized acrylic resin emulsion of each example were as shown in Table 7.

[0046]

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[0047]

The acrylic silicone emulsion composition of the present invention comprises a (meth) acrylate monomer (1)
60 to 97% by weight, α, β-unsaturated carboxylic acid (2) 1
Acrylic resin emulsion (A) 20 obtained by emulsion polymerization of a monomer mixture comprising 10 to 10% by weight, a polymerizable emulsifier (3) 1 to 10% by weight, and a polymerizable light stabilizer (4) 1 to 20% by weight. -99% by weight, 0-30% by weight of an organoalkoxysilane compound (B) having at least one glycidyl group in one molecule, and 1-50% by weight of a polymerizable silicone compound (C).

In the acrylic silicone emulsion composition of the present invention, since the acrylic resin emulsion (A) contains a polymerizable light stabilizer, the emulsion has excellent storage stability and chemical resistance. Because it is copolymerized, it has excellent weather resistance over a long period of time.

Further, since the organoalkoxysilane compound (B) having a glycidyl group is used for silicone conversion, the crosslinkability of the acrylic silicone emulsion composition is improved at the time of coating film formation, and the chemical resistance of the coating film is improved. The stain resistance, hardness, and scratch resistance are excellent. Further, since the polymerizable silicone compound (C) is used, this effect is backed up and guaranteed. Further, since the polymerizable silicone compound (C) is mixed, the storage stability of the acrylic silicone emulsion composition is dramatically improved. Further, it is possible to lower the film forming temperature, and it is possible to minimize the amount of an organic solvent that deteriorates the performance of a film such as a film forming agent. Therefore, when the acrylic silicone emulsion composition of the present invention is used as a coating resin, a coating film having excellent weather resistance, stain resistance and water resistance can be obtained. Also, since the base of the acrylic silicone emulsion composition is water, the safety is high,
It will be environmentally friendly.

Claims (6)

[Claims] 1. A (meth) acrylate monomer (1)
60 to 97% by weight, α, β-unsaturated carboxylic acid (2) 1
Acrylic resin emulsion (A) 20 obtained by emulsion polymerization of a monomer mixture comprising 10 to 10% by weight, a polymerizable emulsifier (3) 1 to 10% by weight, and a polymerizable light stabilizer (4) 1 to 20% by weight. Acrylic silicone emulsion composition comprising -99% by weight, 0-30% by weight of an organoalkoxysilane compound (B) having at least one glycidyl group in one molecule, and 1-50% by weight of a polymerizable silicone compound (C). Stuff. 2. The method according to claim 1, wherein the polymerizable emulsifier (3) has an acrylic or allylic functional group and is represented by the formula I or II, but is a single or a mixture of two or more. The acrylic silicone emulsion composition according to the above. Embedded image Embedded image 3. The acrylic silicone emulsion composition according to claim 1, wherein the polymerizable light stabilizer (4) is represented by the formula III. Embedded image 4. The method according to claim 1, wherein the polymerizable silicone compound (C) is a mixture of dimethoxymethylphenylsilane, trimethoxyphenylsilane, and a silicone compound having a reactive functional group at a terminal or a side chain. The acrylic silicone emulsion composition according to claim 1. 5. The acrylic silicone emulsion composition according to claim 4, wherein the weight ratio of volatile component / non-volatile component of the polymerizable silicone compound (C) is from 99/1 to 70/30. 6. A silicone compound having a reactive functional group at a terminal or a side chain represented by the formula IV or V, wherein the functional group is a hydroxyl group, an epoxy group, an amino group, a methoxy group,
The acrylic silicone emulsion composition according to claim 4, comprising a compound having at least one selected from an ethoxy group, an n-propyloxy group, and an i-propyloxy group. Embedded image Embedded image