KR20010058978A - A cure type coating composition for UV - Google Patents

Abstract

PURPOSE: An ultraviolet ray hardening film composition is provided for improving contamination-resistance, chemical-resistance, durability and physical property by reacting isocyanate oligomer and specific chemical structures of compounds and adding modified urethane acrylate oligomers and silicone acrylate. CONSTITUTION: The hardening film composition comprises silicone 10-70 wt.% of modified urethane acrylate oligomer of formula 1 (wherein R1 is hydrogen or methyl group, R2 is (CH2)liter where liter is integer of 1-10, R3 is linear aliphatic, cycloaliphatic, aromatic compounds or oligomer of them, R4 is hydrogen or alkyl or benzyl groups having C1-C4, n is integer of 1-20; Y is silicone intermediate having at least two hydroxyl radicals at its terminal); 10-70 wt.% of polyether polyol modified urethane acrylate oligomer of formula 2 (wherein R has the following formula; R1 to R4 and n has the same meaning to the formula 1; and m+p is integer of 3-12); 10-70 wt.% of reactive monomer; 1-10 wt.% of photo initiator; and 1-10 wt.% of leveling agent.

Description

UV curable coating composition {A cure type coating composition for UV}

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an ultraviolet curable coating film composition, and relates to an ultraviolet curable coating film composition applicable to paper, synthetic resin, wood iron, ordinary wound blackboards, and boards in addition to vinyl chloride sheet.

In terms of use, vinyl chloride flooring is divided into heavy-duty walks and warning walks, which are used in offices, department stores, general stores, gymnasiums, etc., and are UV-curable varnishes early in order to increase abrasion resistance, durability, pollution resistance, and chemical resistance. The UV curable varnish also plays a role in improving the abrasion resistance, durability, stain resistance, and chemical resistance of vinyl chloride floorboards, even for alarm floors used in living rooms, kitchens and bedrooms in apartments and general houses. It was not enough to fully satisfy consumer needs.

It is poorly resistant to contamination, so it cannot be easily removed after contaminants (creon, magic, kimchi soup, oral medicine, etc.) are smeared.It has poor chemical resistance, which causes discoloration of disinfectant, cold medicine, drink, etc., or surface texture in high temperature and high humidity environment. There was a problem that the physical and mechanical properties, such as sticky, are significantly lowered.

Conventional UV curable coating composition is U.S. Pat. 3,932,356 and 4,301,209.

However, the ultraviolet curable coating composition described in the above patents has a disadvantage in that the wear resistance, pollution resistance, durability, moisture resistance is insufficient.

In order to solve the above problems, the present inventors conducted extensive research, and as a result, a silicone-modified urethane acrylic prepared by reacting an isocyanate oligomer with a compound represented by the chemicals 3, 4, 5, 6, and 7 in an ultraviolet curable coating film composition By containing the late oligomer, polyether modified urethane acrylate oligomer and silicone acrylate, it completely compensates for the disadvantages of contamination resistance, chemical resistance, durability and moisture resistance, so it is less absorbed when friction with foreign substances, and contaminants such as magic Even after wiping with a tissue or dry cloth, the stain marks can be easily erased, and it is not polluted by kimchi soup, etc., and has excellent non-pollution properties, and shows good non-pollution resistance even in high temperature and high humidity environments. Completed excellent UV curable coating composition .

Therefore, in the present invention, it has a very excellent non-pollution, durability, moisture resistance, and protects the coating surface, so that memo boards, video screens, wall hangings, etc. based on soft sheets (PVC, paper) among general application products for blackboards in addition to the existing vinyl chloride sheet Applicable to board-like whiteboards that are wound on boards and hard materials (synthetic resin, wood, steel, etc.), that is, event schedules, wall-mounted whiteboards, mobile whiteboards, operational whiteboards, and educational whiteboards. An object thereof is to provide an ultraviolet curable coating film composition.

The ultraviolet curable coating composition of the present invention for achieving the above object is 10 to 40% by weight of the silicone-modified urethane acrylate oligomer represented by the following formula (1), 10 to 40% by weight of the polyether-modified urethane acrylate oligomer represented by the following formula (2) %, 10 to 70% by weight of reactive monomer, 1 to 10% by weight of photoinitiator, and 1 to 10% by weight of leveling agent.

Formula 1

Wherein R ₁ is a hydrogen atom or a methyl group, R ₂ is (CH ₂ ) ₁ (wherein l is an integer of 1 to 10), and R ₃ is a linear aliphatic, cyclic aliphatic having ₄ to 20 carbon atoms, An aromatic compound or an oligomer of these compounds, R ₄ is a hydrogen atom or an alkyl group or benzyl group having 1 to 4 carbon atoms, n is an integer of 1 to 20, and Y is a silicone intermediate having two or more hydroxyl groups at the terminal. to be.

Formula 2

Where R is ego,

R <_1> , R <_2> , R <_3> , R <_4> and n are as above-mentioned, m + p is an integer of 3-12.

The ultraviolet curable coating composition according to the present invention contains a silicone-modified urethane acrylate oligomer represented by the formula (1) and a polyether-modified urethane acrylate oligomer represented by the formula (2) and a silicone acrylate, wherein the photoinitiator, monomer, leveling agent Etc. are included.

(1) Silicone-modified urethane acrylate oligomer represented by formula (1)

The silicone-modified urethane acrylate oligomer represented by Chemical Formula 1 contained in the ultraviolet curable coating film composition according to the present invention hydrosilylates an isocyanate oligomer and a tertiary silane represented by Chemical Formula 3 below, and at the terminal represented by Chemical Formula 4 below. After reacting the silicon intermediate having a hydroxyl group, it is prepared by addition reaction of a hydroxyl group-containing acrylate monomer represented by the following formula (5).

Formula 3

In the above formula, R ₄ is as described above.

Formula 4

Wherein R ₅ is -C ₃ H ₆ OC ₂ H ₄ OH, m is an integer from 1 to 10.

Formula 5

Wherein X is a hydrogen atom or a methyl group, and l is as described above.

At this time, the isocyanate oligomer, tertiary silane, silicone intermediate having a hydroxyl group at the terminal and hydroxyl group-containing acrylate monomer are to be contained in a molar ratio of 1: 0.1: 0.1: 3 to 1: 0.2: 0.5: 2.3, Considering the curability and other cured product properties of the final product, it is recommended to have a molar ratio of 1: 0.1: 0.3: 2.3 to 1: 0.2: 0.4: 2.5. If the content of each component is out of the molar ratio, the curability is slow, there is a problem of poor appearance and feel after curing.

Here, specific examples of isocyanate oligomers include isophorone diisocyanate, 4,4-dicyclohexyl methyl diisocyanate, trimethyl hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,4,4-trimethyl 1,6 hexa Isocyanate groups, such as methane diisocyanate, octadecylene diisocyanate, 2,6-toluene diisocyanate, 1,6 hexamethylene isocyanate oligomer, biuret or isocyanurate, and 2,4,4-toluene diisocyanate 2-20 Any one can be used.

In particular, it is preferable to use isophorone diisocyanate or isocyanurate in view of the application properties of the coating film.

Meanwhile, as the tertiary silane represented by Chemical Formula 3 used in the preparation of the silicone-modified urethane acrylate oligomer of the present invention, benzyl dimethyl silane, butyl dimethyl silane, diethylmethyl silane, 1,1,1,3,3, 5,5, -heptamethyl trisiloxane, isobutyl diethoxy silane, hexyl ethoxy silane, trimethyl silane and the like can be used.

The hydrosilylation of the isocyanate oligomer and the tertiary silane represented by Chemical Formula 3 is carried out by reacting hexachloro platonic acid at 80 to 130 ° C. under a reduced pressure at a pressure of 0.1 to 0.9 atm.

Then, a silicon intermediate having a hydroxyl group is added to the terminal represented by Chemical Formula 4 and reacted.

Examples of the silicon intermediate having hydroxyl groups at the terminal may include dimethyl siloxane, 3-hydroxy propyl-terminated (dimethylated), dimethyl, methyl (propylene oxide) siloxane, and the like.

If necessary, the silicone intermediate having a hydroxyl group at such a terminal may be condensed with unsaturated carboxylic acid at a molar ratio of 1 / 0.95 to 1 / 0.7, but preferably 1 / 0.95 to 1 / 0.85 in consideration of sclerosis. Do.

Meanwhile, the hydroxyl group-containing acrylate monomer represented by Chemical Formula 5 is reacted by dropping a silicon intermediate having a hydroxyl group at the terminal represented by Chemical Formula 4 at 40 to 55 ° C. for 30 minutes to 2 hours. The modified silicone urethane acrylate oligomer represented by the general formula (1) was prepared by addition reaction by adding to and heating to 65 ~ 90 ℃ while paying attention to the exotherm.

Examples of the acrylate monomer having a double bond and a hydroxyl group at these terminals include hydroxy ethyl acrylate, hydroxy ethyl methacrylate, hydroxy propyl acrylate, hydroxy propyl methacrylate, hydroxy butyl methacrylate, and hydroxy. Hydroxy pentyl acrylate, hydroxy pentyl methacrylate, hydroxy hexyl acrylate, hydroxy hexyl methacrylate and the like can be used.

The silicone-modified urethane acrylate oligomer represented by Chemical Formula 1 prepared through the above process has a weight average molecular weight in the range of 1,200 to 40,000, in terms of improving non-pollution persistence and appearance.

The silicone-modified urethane acrylate oligomer represented by Chemical Formula 1 may be used in an amount of 10 to 70% by weight based on the total composition. When the amount is less than the amount, non-pollution, adhesion and appearance are deteriorated. Poor property and a strong coating. It is preferable to use 25-40 weight% in consideration of the physical property of a coating film and the viscosity of a varnish.

(2) Polyether polyol-modified urethane acrylate oligomer represented by formula (2)

In order to achieve another object of the present invention, the UV curable coating composition of the present invention uses a polyether polyol-modified urethane acrylate oligomer represented by Formula 2 as an oligomer, which is an isocyanate oligomer and a polyether polyol represented by the following Formula 6. It is prepared by addition reaction of a hydroxyl group-containing acrylate monomer represented by the formula (5).

In the above formula, R ₄ is as described above.

Wherein R ₅ is -C ₃ H ₆ OC ₂ H ₄ OH, m is an integer from 1 to 10.

Wherein X is a hydrogen atom or a methyl group, and l is as described above.

Formula 6

Where m + p is as described above.

At this time, as the isocyanate oligomer to be used, all of the above-mentioned isocyanate may be used, but isocyanurate is preferably used in consideration of cured product properties.

In addition, as the polyether polyol represented by the formula (6) used for the production of the isocyanate oligomer represented by the formula (2), a polymerized propylene glycol is used and a molecular weight of 200 to 700 is used.

At this time, the molar ratio of isocyanurate / polyetherpolyol / hydroxyl group-containing acrylate monomer is 1 / 0.1 / 1.2 to 1 / 0.8 / 0.5, but considering the moisture resistance, adhesion and curability of the final product, it is 1 / 0.4 / 0.9-1 / 0.6 / 0.7 are more preferable.

The polyether polyol-modified urethane acrylate oligomer represented by the above formula (2) is a double at the terminal represented by the formula (5) after reacting the polyether polyol represented by the formula (6) to the isocyanurate at 40 to 45 ℃ It is prepared by reacting an acrylate monomer having a bond and a hydroxyl group at 60 to 65 ° C.

In addition, the polyether polyol-modified urethane acrylate oligomer represented by Formula 2 may have a weight average molecular weight in the range of 1,000 to 10,000 to improve curability and moisture resistance.

The ultraviolet curable coating composition of the present invention comprising such silicone-modified urethane acrylate and polyether polyol-modified urethane acrylate oligomer comprises a reactive monomer, a photoinitiator, a leveling agent and a silicone acrylate, a quencher and other additives, and has a viscosity of 25 It is a coating film composition which is 500-800 cps at ° C.

The polyether polyol-modified urethane acrylate oligomer represented by Chemical Formula 2 may be used in an amount of 10 to 50% by weight based on the total composition, and when the amount is less than the amount, the non-moisture resistance, the adhesion and the appearance are deteriorated. High workability and poor hardenability. It is preferable to use 25-40 weight% in consideration of the curability of a coating film and the viscosity of a varnish.

(3) reactive monomer

The reactive monomer of the present invention may be polymerized with a silicone-modified urethane acrylate oligomer to affect the physical properties of the coating film, and one or more monomers may be used. The main monomers are acrylic ester monomers and / or monomers having monofunctional vinyl groups. .

It is preferable to use 10 to 70 weight% of such reactive monomers with respect to the whole composition.

The acrylic acid ester is prepared by esterification of an alcohol with an unsaturated carboxylic acid, 1,4-butanediol diacrylate, 1,6 hexanediol diacrylate, neopentyl glycol diacrylate, pentaerythritol trimethacrylate, trimethylol Propane triacrylate, ethyl hexyl acrylate, ethyl hexyl methacrylate, pentyl acrylate, hexyl acrylate, cyclohexyl methacrylate, 1,4-butanediol diacrylate or tripropylene glycol diacrylate, polyethylene glycol diacryl Although there exist a rate etc., it is preferable to use with a silicone-modified urethane acrylate oligomer in 1/8-8/1 weight ratio.

Monomers having a monofunctional vinyl group include N-vinyl-2 pyrrolidone, vinyl acetate, vinyl butyrate, vinyl isobutylate, vinyl caprate, vinyl caproate, vinyl captylate, vinylcetyl ether, and vinylcyclo hexanol , Vinyl-n-decanoate, vinyl octadecyl ether, etc., N-vinyl-2pyrrolidone is useful for adjusting the viscosity of varnish coating and increasing the curing rate. It can be used at 1/7 to 7/1 weight ratio, and it is preferable to use at 1/3 to 3/1 weight ratio.

Since the said reactive monomer is related to the viscosity of a varnish, the softness of a coating film, hardness, adhesiveness, etc., it is good to mix in an appropriate ratio.

(4) photoinitiators

The photoinitiator uses a conventional polymerization initiator activated by ultraviolet rays, and in particular, benzophenone series, benzyldimetal series, acetophenone series, andhraquinone series, thioxanthone series, and the like are used in an amount of 1 to 10% by weight of the whole composition. do.

As the photoinitiator, hydroxy-cyclohexyl phenyl ketone, 2.2-dimethoxy-2-phenyl, acetophenone, benzophenone, or phenyl-2-hydroxy-2phenyl ketone is mainly used.

(5) Leveling agent

As a leveling agent, the compound of silicone type or silicone polyacrylic-type is used at 0.1 to 10 weight% of the whole composition.

When semi-gloss or matte is required for the coating film composition, a matting agent may be used. The silica-based matting agent may be used in an amount of 1 to 10% by weight based on the required gloss.

In particular, the silicone acrylate is prepared by reacting the organo polysiloxane containing an amine group with glycidyl acrylate or glycidyl methacrylate. The molar ratio of the organo polysiloxane / glycidyl (meth) ) Acrylate = 0.8 / 1.05 ~ 1/2, but for improving non-pollution persistence of cured coating film, it is preferred to be within 1 / 1.05 ~ 1 / 1.1 and good non-pollution property when used at 0.5-10% by weight of the total composition. You can expect to improve sustainability.

If the content is used in excess of 10% by weight, the appearance becomes poor, and when used in less than 0.5% by weight it is difficult to expect the improvement of the persistence.

(7) other additives

Other additives can be used by varying the addition amount of known compounds as required.

Although the efficacy and effect of the ultraviolet curable coating film composition of this invention and a vinyl chloride sheet using the same are demonstrated in more detail through the following example and a comparative example, the following example does not limit the scope of the present invention.

<Production of Silicone-Modified Urethane Acrylate Oligomers Represented by Formula 1>

<Manufacture example 1>

564.4 g of isocyanurate oligomer was added to a four-necked round flask, 0.56 g of hexachloro platonic acid was added thereto, and then a condenser, a thermometer, and a stirrer were mounted. The contents were warmed up to 100 ° C., and 43.5 g of benzyl dimethyl silane was slowly added thereto and reacted for 4 hours. At this time, the termination was confirmed using an infrared analyzer. Then, the temperature of the contents was maintained at 45 ° C. and 123 g of dimethyl siloxane and 3-hydroxy propyl-terminated were added thereto, followed by reaction for 1 hour, followed by slowly dropwise addition of 268.8 g of hydroxy propyl acrylate for 30 minutes. I was. At this time, when the non-catalytic reaction was carried out, a silicone-modified urethane acrylate oligomer was prepared at a reaction temperature of 70 ° C. or less.

<Production Example 2>

Silicone modification using the same method as Example 1 using 569.9 g of isocyanurate, 34.0 g of tertiary butyl dimethyl silane, dimethyl siloxane, 124.2 g of 3-hydroxy propyl-terminated and 271.2 g of hydroxy ethyl acrylate Urethane acrylate oligomers were prepared.

<Production Example 3>

Silicone-modified urethane acrylate in the same manner as in Example 1 above using isocyanurate 556.6, benzyl dimethyl silane 34.0 g, dimethyl siloxane, 3-hydroxy propyl-terminated 121.3 g, hydroxy ethyl acrylate 264.9 g Oligomers were prepared.

<Preparation of polyether polyol-modified urethane acrylate oligomer represented by Formula 2>

<Production Example 4>

500 g of isocyanurate was added to a four-round flask, 1 g of DBTDL (Dibutyltin dilaurate) and 3 g of HQ (Hyquinone) were added to the reaction catalyst, and 200 g of polyether polyol (trade name: PPG400, Korea Polyol Co., Ltd.) was added to the dropping panel. It was slowly added dropwise for about 1.5 hours at 25 ℃. At this time, care should be taken in the heat generation so that the reaction temperature does not exceed 45 ℃. At the time of completion of the first reaction, 296 g of hydroxyethyl acrylate was added dropwise to the dropping panel and slowly added dropwise for 30 minutes to maintain a reaction temperature at 60 to 65 ° C to prepare a polyether polyol-modified urethane acrylate.

<Production of Silicone Acrylate>

Production Example 5

Into a four-necked round flask, 257 g of polydimethyl siloxane having a hydroxyl group at the end was added, a thermometer, a condenser and a stirrer were added, and 242 g of 3-ethylenediamino propyl methyl dimethoxy silane was added dropwise for 30 minutes (at this time, the water bath was To control the exotherm) to react at 10 ° C. for 2 hours to prepare an organopolysiloxane having an amine group.

After stirring, 1 g of MEHQ, a polymerization inhibitor, was added thereto, and 500 g of glycidyl acrylate was added dropwise for 10 minutes, and the reaction temperature was raised to 60 to 70 ° C. to prepare a silicon acrylate for 8 hours.

The progress of the reaction was measured using an infrared analyzer.

<Production of UV Curable Coating Composition>

<Example 1>

222 parts by weight of the silicone-modified urethane acrylate oligomer prepared in Preparation Example 1, 222 parts by weight of urethane acrylate (UCB, product name Evercryl 1290), 200 parts by weight of 1,6 hexanediol diacrylate, tripropylene glycol diacryl Rate 66 parts by weight, 240 parts by weight of neopentyl glycol diacrylate, 40 parts by weight of Darocure 1173 (CIBA-GEIGY) as a photoinitiator, (UCB company, product name Evercryl 350 as a leveling agent) 10 parts by weight was added, and the mixture was stirred at 40 ° C to obtain an ultraviolet curable coating film composition containing a silicone-modified urethane acrylate oligomer having a viscosity of 800 cps at 25 ° C.

<Example 2>

A UV curable coating film composition containing a silicone-modified urethane acrylate oligomer was obtained in the same composition and method as in Example 1 except that the silicone-modified urethane acrylate oligomer prepared in Preparation Example 2 was used.

<Example 3>

A UV curable coating film composition containing a silicone-modified urethane acrylate oligomer was obtained in the same composition and method as in Example 1 except that the silicone-modified urethane acrylate oligomer prepared in Preparation Example 3 was used.

<Example 4>

The silicone-modified urethane acrylate oligomer prepared in Preparation Example 1 was used, and the silicone acrylate prepared in Preparation Example 5 was used instead of the leveling agent used in Example 1 (UCB, product name Evercryl 350). The ultraviolet curable coating film composition containing the silicone-modified urethane acrylate oligomer was obtained by the same composition and method as Example 1.

Example 5

The above-mentioned procedure was carried out except that the silicone modified urethane acrylate oligomer prepared in Preparation Example 2 was used and the silicone acrylate prepared in Preparation Example 5 was used instead of the leveling agent (UCB, product name Evercryl 350) used in Example 1. The ultraviolet curable coating film composition containing the silicone-modified urethane acrylate oligomer was obtained by the composition and method similar to Example 1.

<Example 6>

The silicone modified urethane acrylate oligomer prepared in Preparation Example 3 was used, and the silicone acrylate prepared in Preparation Example 5 was used instead of the leveling agent used in Example 1 (UCB, product name Evercryl 350). The ultraviolet curable coating film composition containing the silicone-modified urethane acrylate oligomer was obtained by the composition and method similar to Example 1.

<Example 7>

222 parts by weight of the silicone-modified urethane acrylate oligomer prepared in Preparation Example 1 and 222 parts by weight of the polyether polyol-modified urethane acrylate prepared in Preparation Example 2, the leveling agent used in Example 1 (UCB, UV curable coating film containing a silicone-modified urethane acrylate oligomer and polyether polyol-modified urethane acrylate in the same composition and method as in Example 1 except that the silicone acrylate prepared in Preparation Example 5 was used instead of the product name Evercryl 350). A composition was obtained.

<Comparative Example 1>

Except that 222 parts by weight of the silicone-modified urethane acrylate oligomer (prepared in Preparation Example 1) and 222 parts by weight of urethane acrylate (UCB, product name Evercryl 1290) of Example 1 except for using only 444 parts by weight of urethane acrylate An ultraviolet curable coating film composition was prepared in the same composition and method as in Example 1.

Experimental Example

Non-pollution properties of the UV curable coating composition prepared in Examples 1 to 7 and Comparative Examples were measured, and the results are shown in Table 1 below, and the cured materials were measured and the results are shown in Table 2 below.

Non-contamination was observed after 24 hours after contaminated with oily magic (black) and wiped off with toilet paper to observe the traces. Wear resistance was measured using the Teledyne Taber Model 505 after 250 revolutions and 500 revolutions. Slipability was measured by ASTM D4518 on the coated hardened surface.

Black magic Blue Magic Red magic Grape juice Fanta Cola Kimchi soup Soy sauce iodine crayon Persistence Example 1 One One One One One One One One One One 100 times Example 2 One One One One One One One One One One 120 times Example 3 One One One One One One One One One One 140 times Example 4 One One One One One One One One One One 200 times Example 5 One One One One One One One One One One 240 times Example 6 One One One One One One One One One One 240 times Example 7 One One One One One One One One One One 240 times Comparative Example 1 5 5 5 5 3 One 3 One 5 One 0 times

In Table 1, the non-pollution property was observed by wiping with toilet paper after 24 hours after contamination with oily magic (black), and the better as 1, the poorer as 5. 1 indicates that no trace of contamination remains, and the paint is tested by applying 8% of a matting agent, and the persistence describes a time when no trace remains by wiping with a tissue after contamination with black magic.

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Comparative Example 1 Zhejiang Good Good Good Good Good Good Good Good Abrasion resistance (mg loss) 250 turns 5 6 7 5 4.5 4.8 4.5 8 500 turns 6 6.2 6.1 4.3 4.7 4.9 4.7 9 1000 turns 7 7.1 7.3 5.3 52 5.0 4.8 11 Slip 45 46 45 46 47 46 45 50

In Table 2, storage property was observed at room temperature after the paint was prepared at room temperature, and wear resistance was visually observed. Wear resistance was measured using the Teledyne Taber model 505 after 250, 500, and 1000 mg. Slipability is measured according to ASTM D4518 on coated dry surfaces.

As described in detail above, the UV-curable coating composition of the present invention completely compensates for the disadvantages of non-pollution, chemical resistance, and durability, and is less scratched when rubbed with a foreign substance, even after contact with a contaminant such as magic or the like. It can be easily removed by wiping with a rag, etc. It is not contaminated with kimchi soup and has excellent non-pollution properties. It is also excellent in chemical resistance, durability and physical properties. It can be used for paper, synthetic resin, wood, steel, and ordinary paper. Applicable for double-strength blackboards and boards.

Claims (9)

10 to 70% by weight of the silicone-modified urethane acrylate oligomer represented by the following formula (1), 10 to 70% by weight of the polyether polyol-modified urethane acrylate oligomer represented by the following formula (2), 10 to 70% by weight of the reactive monomer, photoinitiator 1 to 10 An ultraviolet curable coating film composition containing 1% by weight and 1 to 10% by weight of a leveling agent. Formula 1 Wherein R ₁ is a hydrogen atom or a methyl group, R ₂ is (CH ₂ ) ₁ (wherein l is an integer of 1 to 10), and R ₃ is a linear aliphatic, cyclic aliphatic having ₄ to 20 carbon atoms, An aromatic compound or an oligomer of these compounds, R ₄ is a hydrogen atom or an alkyl group or benzyl group having 1 to 4 carbon atoms, n is an integer of 1 to 20, and Y is a silicon intermediate having two or more hydroxyl groups at the terminal. to be. Formula 2 Where R is ego, R <_1> , R <_2> , R <_3> , R <_4> and n are as above-mentioned, m + p is an integer of 3-12. According to claim 1, wherein the silicone-modified urethane acrylate oligomer represented by the formula (1) is hydrosilylation of the isocyanate oligomer and the tertiary silane represented by the following formula (3), the hydroxyl group at the terminal represented by the following formula (4) After reacting more than one silicon intermediate having a UV curable coating composition, characterized in that prepared by the addition reaction of the hydroxyl group-containing acrylate monomer represented by the formula (5). Formula 3 In the above formula, R ₄ is as described above. Formula 4 Wherein R ₅ is -C ₃ H ₆ OC ₂ H ₄ OH, m is an integer from 1 to 10. Formula 5 Wherein X is a hydrogen atom or a methyl group, and l is as described above. The polyether polyol-modified urethane acrylate oligomer of claim 1, wherein the polyether polyol-modified urethane acrylate oligomer represented by the addition of a polyether polyol represented by the following formula (6) and a hydroxyl group-containing acrylate monomer represented by the formula (5) isocyanate oligomer UV-curable coating film composition characterized in that it is prepared by. Formula 6 Where m + p is as described above. The UV curable coating composition further comprises 1 to 10% by weight of a silicone acrylate prepared by reacting an organic polysiloxane containing an amine group with a glycidyl acrylic compound represented by the following formula (7): UV curable coating film composition. Formula 7 X is as described above. The UV curable coating composition according to claim 2 or 3, wherein the isocyanate oligomer is 2 to 20 isocyanate groups. 3. The tertiary silane of claim 2 is benzyl dimethyl silane, butyl dimethyl silane, diethylmethyl silane, 1,1,1,3,3,5,5, -heptamethyl trisiloxane, isobutyl diethoxy UV-curable coating composition, characterized in that at least one member selected from the group consisting of silane, phenyl dimethyl silane, hexyl dimethoxy silane and trimethyl silane. 3. The silicone intermediate according to claim 2, wherein the silicone intermediate having at least two hydroxyl groups at the terminal is at least one selected from the group consisting of dimethyl siloxane, 3-hydroxy propyl-terminated and dimethyl, methyl (propylene oxide) siloxane. UV curable coating film composition. A vinyl chloride sheet coated with the ultraviolet curable coating composition of claim 1. A wound or board blackboard coated with the ultraviolet curable coating composition of claim 1.