KR101403067B1 - Ultraviolet-curable coating material composition and hard coating film by employing the same - Google Patents

Abstract

The present invention relates to an ultraviolet curable coating composition and a method of controlling hardness of a coating film using the same. Specifically, the present invention can provide a coating film comprising a multi-vinyl organosiloxane having a high hardness, an excellent weather resistance and an antifouling property, and simply controlling the content of the vinyl group of the polyvinyl polyorganosiloxane, Can be controlled.

Description

[0001] The present invention relates to an ultraviolet curable coating composition,

The present invention relates to an ultraviolet ray curable coating composition and a process for producing a high hardness coating film using the same. Specifically, the present invention can provide a coating film containing a multi-vinyl organosiloxane having high hardness, excellent weather resistance, and antifouling property, and by controlling the vinyl group content of the polyvinyl polyorganosiloxane simply, a high hardness Can be controlled.

Hard coatings are used for surface protection of contamination-critical products such as liquid crystal displays (LCDs), plasma displays (PDPs), solar panels, light emitting displays (EL) Fingerprints, markers, and / or ease of removal (i.e., antifouling). The hard coating method uses a method of applying the prepared hard coating agent to obtain a coating film.

Conventionally, a curing method using heat has been widely used. However, a method of curing using heat is slow in production speed and a large amount of solvent is used to influence environmental pollution, so that a curing method for replacing the curing method is increasing.

 Recently, a method of curing using ultraviolet (UV) has been widely used as a curing method that replaces the method using heat. The curing method using ultraviolet rays cures a coating material in a short time by using ultraviolet rays, .

As the UV curing coating compound which is widely used in the past, a large amount of acrylic compound, urethane acrylic compound or epoxy compound has been mainly used, but there is a problem in obtaining a coating film having poor weatherability and chemical resistance and also having self-purification and antifouling properties.

It is an object of the present invention to solve the above problems of the prior art and to provide a high hardness coating film without being harmful to the environment and to easily control the hardness of the coating film and to produce various coating films depending on the product to which the coating film is applied Curable < / RTI > coating composition.

It is another object of the present invention to provide a method for controlling the hardness of a hard coating film.

In order to accomplish the object of the present invention, the present invention provides an ultraviolet curable coating composition characterized in that the multi-vinyl group polyorganosiloxane represented by the general formula (1) is a main component.

[Chemical Formula 1]

(Wherein R < ₁ > To R < ₇ > independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 10 carbon atoms, and do not include O, N, or S; n and m are integers from 3 to 300, n + m is from 6 to 600, and the molar ratio of n: m is from 1: 1 to 5).

In order to accomplish still another object of the present invention, there is provided a process for preparing a cyclic siloxane according to the present invention, comprising the steps of: controlling the molar ratio of the cyclosiloxane of the formula (2), the cyclosiloxane of the formula (3) And polymerizing the siloxane mixture at 80 to 100 ° C for 1 to 10 hours. The present invention also provides a method for controlling the vinyl group content of the polyvinylpolyorganosiloxane of Formula (1).

(2)

(3)

[Chemical Formula 4]

(Wherein R < ₁ > To R ₇ are independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 10 carbon atoms, and do not include O, N, or S).

In order to accomplish still another object of the present invention, the present invention provides a method for producing a vinyl-containing copolymer, which comprises polymerizing, while controlling the molar ratio of the cyclosiloxane of formula (2), the cyclosiloxane of formula (3) Preparing a polyol organosiloxane; Preparing an ultraviolet curable coating composition comprising the multi-vinyl-group polyorganosiloxane of Formula 1; And irradiating ultraviolet light onto the ultraviolet curable coating composition to produce a coating film.

Since the coating composition according to the present invention uses ultraviolet curing, it is faster than the existing heat curing type and has less environmental pollution than the existing acrylic ultraviolet curing type.

In addition, a coating film made of a coating composition having a polyvinyl group-containing polyorganosiloxane as a base resin has a hardness superior to that of a conventional coating film, and thus the product can be safely protected from foreign substances and impacts.

In addition, since it is coated with a material containing silicon, it is excellent in weatherability and antifouling properties, and the hardness of a coating film to be formed can be controlled by simply controlling the vinyl group content of the polyorganosiloxane. Therefore, a flexible coating film is required The hardness of the coating film can be easily controlled according to the characteristics of the product, so that it can be applied to various application fields.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 shows NMR results of a multi-vinyl-group polyorganosiloxane prepared according to the present invention.
2 is a graph showing the transparency according to the vinyl group content according to the present invention.

Hereinafter, the present invention will be described more specifically. It should be understood, however, that this is for the purpose of promoting understanding of the invention and should not be construed as limiting the scope of the invention.

≪ UV curable coating composition >

The present invention provides an ultraviolet curable coating composition characterized in that it is based on a polyorganosiloxane containing a multi-vinyl group of the general formula (1).

[Chemical Formula 1]

Wherein R ₁ to R ₇ independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 1 to 10 carbon atoms and not including O, N, and S; m is an integer of 3 to 300, n + m is 6 to 600, and a molar ratio of n: m is 1: 1 to 5).

In one embodiment of the present invention, the multivinyl group polyorganosiloxane has a weight average molecular weight ranging from about 500 to 30,000. If it is less than 500, the coating film becomes weak. If it is more than 30,000, high hardness may be a problem.

According to one embodiment of the present invention, the multivinylated organosiloxane is present in the coating composition of the present invention in an amount of 10 to 50% by weight. All weight percentages are based on the total weight of the coating composition.

<Acrylate Monomer>

The coating composition according to the present invention comprises 5 to 15% by weight of a (meth) acrylic monomer.

The (meth) acrylate monomer may be at least one selected from the group consisting of methylmethacrylate (also referred to as methyl methacrylate or methyl methacrylate), ethylmethacrylate, 2-hydroxyethyl methacrylate Substituted or unsubstituted aliphatic C 1-12 alkyl methacrylates such as 2-hydroxyethyl methacrylate, butyl methacrylate and 2-ethylhexyl methacrylate [alkyl methacrylate or alkyl methacrylate Also known as klyric acid]; Substituted or unsubstituted alicyclic C1-12 alkyl methacrylates such as cyclohexyl methacrylate; Substituted or unsubstituted aromatic C6-12 aryl methacrylates such as phenyl methacrylate and benzyl methacrylate; Methyl acrylate (also referred to as methyl acrylate or methyl acrylate), ethyl acrylate, 2-hydroxyethylacrylate, butyl acrylate, and 2-hydroxyethyl acrylate. Substituted or unsubstituted aliphatic C 1-12 alkyl acrylates such as 2-ethylhexyl acrylate and the like [also called alkyl acrylate or alkyl acrylate]; Substituted or unsubstituted alicyclic C1-12 alkyl acrylates such as cyclohexyl acrylate; And substituted or unsubstituted aromatic C 6-12 aryl acrylates such as phenyl acrylate and benzyl methacrylate, and preferably at least one selected from the group consisting of aliphatic C1, such as methyl methacrylate -12 alkyl methacrylate alone or a mixture of C1-12 alkyl methacrylate and other (meth) acrylate monomers as described above.

According to one embodiment of the present invention, when the (meth) acrylate monomer is a mixture of C1-12 alkyl methacrylate and another (meth) acrylate monomer, it is preferable that the amount of the C1-12 alkyl methacrylate is 5 wt% By weight, preferably 7 to 10% by weight. This is because a flexible coating film must be obtained.

< Photoinitiator >

According to one embodiment of the present invention, the ultraviolet curable coating composition according to the present invention comprises 5 to 10% by weight of a photoinitiator.

If the content of the polymerization initiator is lower than the above lower limit, the curing reaction does not progress sufficiently and the desired hardness can not be obtained. On the other hand, when the content of the polymerization initiator is more than the upper limit, there is a disadvantage that the prepared coating layer is colored and inhomogeneous hardness is issued.

The photoinitiator is not particularly limited as long as it can initiate a polymerization reaction through ultraviolet irradiation or the like, and examples thereof include α-hydroxy ketone compounds such as IRGACURE 184, IRGACURE 500, IRGACURE 2959, DAROCUR 1173, (My)); Phenylglyoxylate-based compounds (ex IRGACURE 754, DAROCUR MBF; Ciba Specialty Chemicals); Benzyldimethylketal compounds (ex IRGACURE 651; Ciba Specialty Chemicals); α-aminoketone-based compounds (ex IRGACURE 369, IRGACURE 907, IRGACURE 1300, Ciba Specialty Chemicals); Monoacylphosphine based compounds (MAPO) (ex. DAROCUR TPO; Ciba Specialty Chemicals); Bisacylphosphine compounds (BAPO) (ex IRGACURE 819, IRGACURE 819DW; Ciba Specialty Chemicals); Phosphine oxide-based compounds (ex IRGACURE 2100; Ciba Specialty Chemicals); Metallocene compounds (ex IRGACURE 784; Ciba Specialty Chemicals); Iodonium salt (ex IRGACURE 250 from Ciba Specialty Chemicals); And mixtures of one or more of the above (e.g., DAROCUR 4265, IRGACURE 2022, IRGACURE 1300, IRGACURE 2005, IRGACURE 2010, IRGACURE 2020, Ciba Specialty Chemicals). In the present invention, one or more of the above can be used, but the present invention is not limited thereto.

<Curing agent>

According to one embodiment of the present invention, at least one of the curing agents may be used as needed. The ultraviolet curable coating composition according to the present invention may comprise 30 to 50% by weight of the above-mentioned curing agent.

This curing agent will be described mainly with reference to radically polymerizable monomers and crosslinking agents which are preferable as curing agents.

- Radical Polymerizable Monomer -

As the radical polymerization monomer, a compound having an ethylenic unsaturated group which has a boiling point of 100 占 폚 or higher at atmospheric pressure and which is capable of at least one addition polymerization is preferable. As the ethylenic unsaturated group, a (meth) acryloyl group is particularly preferable.

Further, (meth) acryloyl represents acryloyl or methacryloyl, and similarly, in the following, (meth) acrylate represents acrylate or methacrylate.

Examples of the radically polymerizable monomer having a (meth) acryloyl group include monofunctional acrylates such as polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate and phenoxyethyl (meth) Acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexanediol (meth) acrylate, trimethylol propane tri (acryloyloxypropyl) ether, tri (acryloyloxyethyl ) Ethylene oxide or propylene oxide is added to a polyfunctional alcohol such as isocyanurate, glycerin or trimethylolethane. (Meth) acrylates after acrylic acid, acrylonitrile-butadiene-styrene (meth) acrylate, acrylonitrile-butadiene-styrene (meth) acrylate, Polyester acrylates, epoxy acrylates and the like, which are reaction products of an epoxy resin with (meth) acrylic acid, and the like, as disclosed in Japanese Patent Application Laid-Open No. 48-64183, Japanese Patent Publication No. 49-43191 and Japanese Patent Publication Polyfunctional acrylates or methacrylates; and mixtures thereof. Further, there are exemplified those which have been introduced as photo-curable monomers and oligomers in Japan Adhesion Society Vol. 20, No. 7, pages 300 to 308.

Of these, pentaerythritol tetra (meth) acrylate is preferable, and pentaerythritol pentaacrylate ester is particularly preferable.

<Coating Distribution dealer >

The dispersion medium of the coating composition according to the present invention may be any of those conventionally used in the art, for example, ketones such as methyl ethyl ketone, cyclohexanone, etc., toluene, xylene, tetramethylbenzene, etc. Aromatic hydrocarbons; Glycol ethers such as methyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether and the like; Esters such as ethyl acetate, butyl acetate, acetates of the above-mentioned glycol ethers and the like; Alcohols such as ethanol, propanol, ethylene glycol, propylene glycol and the like; Aliphatic hydrocarbons such as octane, decane and the like, and petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, naphtha solvents and the like.

The diluent may be used alone or as a mixture. The composition according to the invention may contain up to 30%, preferably from 10 to 30% diluent.

By adding a photopolymerizable vinyl monomer as a diluent to the composition according to the present invention, not only the viscosity of the composition can be reduced but also the photopolymerization reaction rate can be increased at the same time.

< Of a multi-vinyl polyorganosiloxane  Manufacturing>

According to an embodiment of the present invention, the polyvinylpolyorganosiloxane of Formula 1 may be prepared by controlling the molar ratio of the siloxane of Formula 2, the siloxane of Formula 3, and the siloxane of Formula 4; And polymerizing the siloxane mixture at 80 to 100 DEG C for 1 to 10 hours.

(2)

(3)

[Chemical Formula 4]

(Wherein R ₁ to R ₇ are independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 1 to 10 carbon atoms and not O, S or N).

<Catalyst>

The polymerization reaction is generally carried out in the presence of a catalyst. Examples of suitable catalysts include, but are not limited to, carboxylic acids (where appropriate in combination with quaternary ammonium salts thereof), compounds of the general formula XSO3H where X is alkyl, aryl, alkaryl or halogen, Secondary and tertiary alkylamines, alkylsulfonium silanolates, alkali metal oxides, hydroxides, alkoxides, quaternary ammonium silanolates and phosphonium compounds, and the like. Preferred catalysts for the process of the present invention are alkali metal oxides, hydroxides, alkoxides and silanolates, particularly preferred are sodium hydroxide, potassium hydroxide, sodium trimethylsilanolate, potassium trimethylsilanolate and tetramethylammonium silanolate TMAS).

These catalysts may be used alone or in combination.

< Of a multi-vinyl polyorganosiloxane Vinyl group  Control of content>

The vinyl group content of the polyvinyl group-containing polyorganosiloxane of formula (1) prepared by varying the molar ratio of the siloxane of formula (3) and the siloxane of formula (4) varies.

That is, as the molar ratio of the formula (4) increases, the molar ratio of m to n in the formula (1) increases and the vinyl group content of the polyvinyl polyorganosiloxane increases.

< Of the coating film  Manufacturing>

The coating composition prepared according to the present invention is applied to a surface which needs to be protected from external impacts or foreign matter, and then irradiated with ultraviolet rays.

The coating composition may be coated by applying a coating solution using a dip coating method, an air knife coating method, a curtain coating method, a roller coating method, a wire bar coating method, a gravure coating method or a die coating method And it is preferable to use the wire bar method.

The thickness of the coating film can be appropriately adjusted according to the properties of the product and the protective property, and is preferably 2 to 15 탆.

The ultraviolet rays used for curing the coating layer obtained after applying and preferably drying the coating composition can be appropriately selected depending on the kind of the polymerization initiator and the curable composition to be used. In the present invention, irradiation with ultraviolet rays is performed, so that the polymerization is quick, the required facilities are compact, and the cost can be reduced.

Examples of the ultraviolet ray include ultrahigh pressure mercury lamp, high pressure mercury lamp, low pressure mercury lamp, carbon arc, xenon arc, metal halide lamp, and the like. The dose of ultraviolet rays is preferably 70 to 180 mJ / cm 2, more preferably 130 to 160 mJ / cm 2.

< Of the coating film  Hardness control>

The hardness of the resulting coating film changes as the vinyl group content of the multi-vinyl-group polyorganosiloxane used as the main component of the coating composition changes.

That is, since the hardness of the coating film is increased due to the dense crosslinking reaction between the vinyl group of the polyvinyl group-containing polyorganosiloxane and the double bond of the curing agent, the hardness of the coating film can be controlled if the vinyl group content of the polyvinyl group polyorganosiloxane can be controlled It is.

Hereinafter, the structure and operation of the present invention will be described in more detail with reference to preferred embodiments of the present invention. It is to be understood, however, that the same is by way of illustration and example only and is not to be construed in a limiting sense.

The contents not described here are sufficiently technically inferior to those skilled in the art, and a description thereof will be omitted.

In the preparation of the coating composition of the present invention, specific constituents of the components used in Examples and Comparative Examples described later are as follows.

(a) Siloxane compound: Gelest reagent was used.

(b) Catalyst: Industrial use of HRS was used.

(c) Photoinitiator: Industrial use of Ciba Co. was used.

(d) Hardener: Sartomer's reagent was used.

(e) Coating dispersant:. SAMCHUN reagent was used.

< Polyvinyl group-containing polyorganosiloxane  Manufacturing>

Manufacturing example  1 to 5:

Hexamethylcyclotrisiloxane, 1,3,5-trimethyltrivinylcyclotrisiloxane and 1,3-divinyltetramethyldisiloxane (VMS) were added to a 300 ml four-necked flask equipped with a reflux condenser, a stirrer, a thermometer and a nitrogen inlet The catalyst, tetramethylammonium silanolate (TMAS), was added in an amount of 0.2 wt% based on the reaction mixture, and the mixture was subjected to equilibration polymerization at 90 ° C for 2 hours under a nitrogen stream.

After the reaction was completed, the temperature of the reaction product was raised to 120 ° C, and the reaction catalyst TMAS was deactivated and removed. The reaction product was added to a vacuum evaporator under reduced pressure and vacuum distillation was conducted to remove unreacted materials and cyclic compounds to obtain a multi-vinylpolyorganosiloxane having different unit proportions of dimethylsiloxane and methylvinylsiloxane (yield: 92%).

Reactant Mole ratio TMAS
(g) Hexamethylcyclotrisiloxane
(g) 1,3,5-trimethyltrivinyltrisiloxane (g) 1,3-divinyltetramethyldisiloxane
(g) Production Example 1 11.123 2.584 18.639 5: 1: 10 0.064 Production Example 2 11.123 5.169 18.639 5: 2: 10 0.069 Production Example 3 11.123 7.754 18.639 5: 3: 10 0.075 Production Example 4 11.123 10.339 18.639 5: 4: 10 0.080 Production Example 5 11.123 12.924 18.639 5: 5: 10 0.085

The NMR results of the multi-vinyl-group polyorganosiloxanes obtained in Production Examples 1 to 5 are shown in Fig.

Production Example 6

15.5 g of hexafluoroethylcyclotrisiloxane was used instead of hexamethylcyclotrisiloxane and 10.5 g of 1,3,5-trifluoroethyltrivinyltrisiloxane was used instead of 1,3,5-trimethyltrivinyltrisiloxane , A polyvinylpolyorganosiloxane was prepared in the same manner as in Production Example 1.

Production Example 7

Except that 15.5 g of fluorophenylcyclotrisiloxane was used instead of hexamethylcyclotrisiloxane and 10.5 g of 1,3,5-trifluorophenyltrivinyltrisiloxane was used instead of 1,3,5-trimethyltrivinyltrisiloxane , A polyvinylpolyorganosiloxane was prepared in the same manner as in Production Example 1. [

&Lt; Preparation of coating composition >

Example  1 to 5: Of a multi-vinyl polyorganosiloxane Vinyl group  Change in content

7.5 g of the polyvinyl polyorganosiloxane prepared in Preparation Examples 1 to 5 and 2.5 g of methyl methacrylate (MMA) as an acrylic monomer were mixed with 20 ml of ethanol, 9 g of dipentaerythritol pentaacrylate ester as a curing agent, 1.33 g (7 wt%) of Irgaure 184 was added and mixed at room temperature to prepare coating solutions of Examples 1 to 5, respectively.

Example  6 to 10: Acrylic monomer  Change in content

The coating compositions of Examples 6 to 10 were prepared by using the multi-vinyl polyorganosiloxane of Production Example 5 and varying the content of acrylate monomers to 1 g, 2.5 g, 4 g, 5.5 g, and 7 g, respectively.

Comparative Example 1: Use of a general polyorganosiloxane containing no multivinyl group

A polyorganosiloxane was prepared in the same manner as in Production Example 1, except that hexamethylcyclotrisiloxane was used instead of 1,3,5-trimethyltrivinylcyclotrisiloxane. The coating composition was prepared in the same manner as in Example 1 Respectively.

Comparative Example  2:

A coating composition was prepared in the same manner as in Comparative Example 1, except that 2-hydroethyl methacrylate (2-HEMA) was used instead of methyl methacrylate as the acrylate monomer.

Comparative Example  3: Heterogeneous atom-containing Siloxane  use

The coating composition was prepared in the same manner as in Example 1, except that 1-butanoic-4-amidopropyl polydimethylsiloxane was used.

< Of the coating film  Manufacturing>

Example  11 to 20 and Comparative Example  4 to 6

The coating compositions prepared in Examples 1 to 10 and Comparative Examples 1 to 3 were washed with acetone, applied on a dry glass plate to a thickness of 20 탆, placed in a reflux dryer, and dried at 130 캜 for 1 minute to remove the solvent. In a UV irradiation apparatus having a wavelength of 80 mW / cm &lt; 2 &gt; for 30 seconds to obtain a cured coating film. A light irradiation apparatus (Model: Dae Ho Company, CURE ZONE 2) used for light irradiation was used.

<Experiment>

Experimental Example  One: Of the coating film  Hardness

The surface hardness of the coating films prepared according to Examples 11 to 20 and Comparative Examples 4 to 6 was measured using a pencil hardness tester and the results are shown in Table 2.

Experimental Example  2: Transmission

The transmittance was measured in the wavelength range from 300 to 800 nm using the UV-Visible spectrum. The results are shown in Table 2 and FIG.

Surface hardness
(500 g) Permeability
(at 365 nm) Example 11 4H 89.21 Example 12 4H 89.74 Example 13 5H 90.36 Example 14 6H 91.27 Example 15 6H 91.83 Example 16 3H 86.58 Example 17 3H 88.78 Example 18 4H 89.86 Example 19 3H 87.56 Example 20 3H 87.56 Comparative Example 4 3H 85.59 Comparative Example 5 3H 86.54 Comparative Example 6 3H 86.48

From FIG. 1, it can be seen that more vinyl groups are shown in Example 5 where the content of vinylsiloxane of Chemical Formula 4 is increased. Therefore, it is possible to easily control the content of the vinyl group of the polyorganosiloxane, which is simply produced by adjusting the molar ratio of the cyclosiloxane of the general formula (3) to the cyclosiloxane of the general formula (4).

Also, from Table 2 and FIG. 2, it can be seen that the hardness of the coating film of Example 15 prepared from the coating composition of Example 5 containing polyvinylpolysiloxane having an increased vinyl group content is lower than that of the coating film having a relatively low vinyl group content It can be seen that the hardness is higher than that of the coating film of Example 11 prepared from the coating composition of Example 1 containing the multi-vinyl polyorganosiloxane.

Further, even when the same multi-vinylpolyorganosiloxane is used, it can be seen that the hardness of the coating film is increased as the content of the monomer of the acrylate is increased.

2 and Table 2, it can be seen that the transparency of the coating film increases as the content of vinyl groups increases.

From these results, it can be seen that the hardness and transparency of the coating film can be easily controlled by controlling the vinyl group content of the polyvinylpolysiloxane.

In addition, the vinyl group content of the polyvinylpolyorganosiloxane can be controlled simply by controlling the relative molar ratio of the cyclosiloxanes of formulas (3) and (4).

Therefore, according to the present invention, it is possible to produce a coating composition capable of producing a coating film having high hardness by a simple process while being environmentally friendly and rapidly curing.

In addition, since the hardness and transparency of the coating film can be easily controlled, the coating film can be freely modified and used depending on the properties and kinds of the product, so that its application field can be broadened.

Claims (10)

An ultraviolet curable coating composition characterized by comprising a polyorganosiloxane containing a multivinyl group of the formula (1) and further comprising an acrylic monomer.
[Chemical Formula 1]

Wherein R ₁ to R ₇ independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 1 to 10 carbon atoms and not including O, N, or S; m is an integer of 3 to 300, n + m is 6 to 600, and a molar ratio of n: m is 1: 1 to 5). The method according to claim 1,
Wherein R &lt; ₁ &gt; to R &lt; ₇ &gt; are substituted with halogen. The method according to claim 1,
Wherein the UV curable coating composition comprises 10 to 50% by weight of a polyorganosiloxane containing a multi-vinyl group of the formula (1). The method according to claim 1,
Characterized in that it comprises 10 to 50% by weight of a polyvinylpolyorganosiloxane of the formula 1, 5 to 15% by weight of an acrylic monomer, 5 to 10% by weight of a photoinitiator and 30 to 50% by weight of a polyfunctional acrylate as a curing agent. Curable coating composition. A hard coat film produced by using the UV curable coating composition of any one of claims 1 to 4. Polymerizing a vinyl siloxane of the formula (2), a cyclosiloxane of the formula (3) and a cyclosiloxane of the formula (4) while controlling the molar ratio to prepare a multivinyl group polyorganosiloxane of the formula (1) whose vinyl group content is controlled;
Preparing an ultraviolet curable coating composition comprising the multi-vinyl-group polyorganosiloxane and the acrylic monomer of Formula 1; And
And irradiating the ultraviolet curable coating composition with ultraviolet light to prepare a coating film.
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

Wherein R ₁ to R ₇ independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 10 carbon atoms and not O, N, or S; n And m is an integer from 3 to 300, n + m is from 6 to 600 and the molar ratio of n: m is from 1: 1 to 5). The method according to claim 6,
Wherein the molar ratio of the siloxane of formula (4) is in proportion to the hardness of the coating film. The method according to claim 6,
The ultraviolet curable coating composition comprises 10 to 50% by weight of a polyvinyl group-containing polyorganosiloxane of the formula (1), 5 to 15% by weight of an acrylic monomer, 5 to 10% by weight of a photoinitiator and 30 to 50% by weight of a polyfunctional acrylate as a curing agent And controlling the hardness of the coating film. delete delete

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