KR101129258B1 - UV curable coating composiition and coating film - Google Patents

Abstract

The present invention relates to a UV curable coating composition and a coating film, and more particularly, to a UV curable functional group-containing binder resin, a UV curable functional group-containing compound, a UV curable silicone graft or block copolymer, a fluorine-based compound, a photoinitiator and a solvent A UV curable coating composition and a coating film.

The UV curable coating composition and coating film of the present invention can prevent contamination adhesion such as fingerprint traces, can be easily removed, and impart contamination resistance and wear resistance at the same time to maintain their properties and at the same time water repellency, water repellency It has excellent oil and antifouling properties and excellent adhesion to the substrate, and can be applied to various substrates such as plastic, metal, glass, and SiO ₂ film.

UV Curing, Fluorine Compound, Pollution Resistance, Wear Resistance

Description

ＵＶ Curable coating composition and coating film {UV curable coating composiition and coating film}

The present invention relates to a UV curable coating composition and a coating film, and more particularly, to a UV curable functional group-containing binder resin, a UV curable functional group-containing compound, a UV curable silicone graft or block copolymer, a fluorine-based compound, a photoinitiator and a solvent A UV curable coating composition and a coating film.

Various displays such as CRTs for monitors, CRTs such as CPTs for TVs, TFT-LCD polarizers, PDP filters, RPTS filters, mobile phone liquid crystals, watches, photographs, picture frames, etc. are closely related to our lives. In order for the display to be resistant to a pollutant, the surface energy is low so that fingerprints and the like do not easily stick, and the charge on the surface flows without being offset or stayed, so that the dust does not adhere to the electrostatic attraction.

Therefore, there have been reported methods of improving the stain resistance to prevent the adhesion of dust and the like by not charging the surface. For example, Japanese Patent Application Laid-Open No. 94-65529 discloses Indium doped Tin Oxide ITO, Antimony-doped Tin Oxide (ATO), Antimony-doped Zinc Oxide (Antimony) Japanese Patent Laid-Open Publication Nos. 93-295353 and 94-32997 disclose a method of using a conductive metal oxide filler such as doped Zinc Oxide (AZO), and a method of using an antistatic agent made of a polymer, and Japanese Patent Laid-Open No. 93 -339336 describes a method of using a low molecular weight surfactant.

However, methods of preventing adhesion of dust and the like by using a conductive metal oxide or a conductive polymer cannot control a low refractive index and thus can not exhibit a low reflection function, and the used surfactant is released to the surface of the coating film with time, so that the effect is long. There is a problem that cannot be sustained.

 Korean Patent Laid-Open Publication Nos. 2004-0083916 and 2004-0085484 describe a coating liquid composition containing a fluorine-based acrylate monomer. However, since the composition is added in a monomer state, polymerization is not performed well because of low reactivity. There was a problem of low. U. S. Patent No. 6,207, 777 describes a coating liquid composition having one component of a polymer composed of repeating units of fluorine-based acrylate, but has a problem of low adhesiveness.

In addition, Macromolucules (2006, 39, 1740-1748), US Patent Publication Nos. 2003-0087338, 2005-0148050, and 2005-0224175 use bioadhesive protein components such as DOPA to improve adhesion. Although a coating liquid composition is described, the patent has a problem of low pollution resistance.

In order to solve the problems of the prior art as described above, an object of the present invention is to provide a UV-curable coating composition and a coating film that can prevent contamination adhesion such as fingerprint traces and can be easily removed.

In addition, the present invention can impart contamination resistance and abrasion resistance at the same time, its properties can be continuously maintained, excellent in water repellency, oil repellency and antifouling properties, and excellent adhesion to the substrate, plastic, metal, glass, SiO ₂ film An object of the present invention is to provide a UV curable coating composition and a coating film that can be applied to various substrates.

In order to achieve the above object, the present invention is a UV-curable functional group-containing binder resin; UV curable functional group containing compound; UV curable silicone grafts or block copolymers; Fluorine compounds; Photoinitiators; And a solvent; provides a UV curable coating composition comprising a.

Preferably, the coating composition is 10 to 80% by weight UV-curable functional group-containing binder resin; 1-30 weight% of UV-curable functional group containing compounds; 1-30% by weight of UV curable silicone graft or block copolymer; 0.01-15 wt% of fluorine-based compounds; 0.1-10% by weight of photoinitiator; And a solvent balance.

In particular, the fluorine-based compound is preferably any one or more selected from perfluoro group-containing acrylates, methacrylates and vinyls having 1 to 6 UV-curable functional groups.

In another aspect, the present invention provides a coating film formed using the coating composition.

The present invention also provides a method for producing a coating film comprising coating the coating composition on a substrate and drying and photocuring the coated coating composition.

In addition, the present invention is an anti-reflection layer (SiO ₂ ), a flat surface CRT, a measuring device lens, a printer head, a PDA touch panel, a mobile phone, a mobile phone window protective cover, a liquid crystal display, an organic light emitting display (OLED) Or a plasma display.

The UV curable coating composition of the present invention can prevent contamination adhesion such as fingerprint traces, can be easily removed, and impart contamination resistance and wear resistance at the same time to maintain its properties continuously. In addition, the coating composition of the present invention is excellent in water repellency, oil repellency and antifouling properties at the same time, excellent adhesion to various substrates such as plastic, metal, glass, SiO ₂ film, TV, notebook, PDA, mobile phone, optical lens, printer head It can be applied to the back.

Hereinafter, the present invention will be described in detail.

The UV curable coating composition according to the present invention is characterized in that it comprises a UV curable functional group-containing binder resin, a UV curable functional group-containing compound, a UV curable silicone graft or block copolymer, a fluorine-based compound, a photoinitiator and a solvent.

The UV curable functional group-containing binder resin used in the present invention functions to impart wear resistance to the coating film of the present invention.

The type of the UV-curable functional group-containing binder resin is not particularly limited as long as it is UV-curable, and specifically, polyfunctional or monofunctional monomers or oligomers such as acrylates, methacrylates and vinyls may be used.

Examples of the acrylates include dipentaerythritol hexaacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, trimethylenepropyltriacrylate, ethylene glycol diacrylate, hexanediol diacrylate, ethyl acrylate and ethylhexyl Acrylate, butyl acrylate, hydroxyethyl acrylate and the like can be used. As an acrylate oligomer, urethane modified acrylate oligomer, epoxy acrylate oligomer, ether acrylate oligomer, etc. are suitable, and 2-6 acrylate functional groups are suitable. At this time, the molecular weight of the oligomer is suitable about 1,000 ~ 10,000.

Further, the methacrylates include trimethylolpropane trimethacrylate, ethylene glycol dimethacrylate, butanediol dimethacrylate, hexaethyl methacrylate, butyl methacrylate, and the like. Can be used.

The vinyls include divinyl benzene, styrene, paramethyl styrene and the like.

The UV curable functional group-containing binder resin is preferably contained in 10 to 80% by weight in the UV curable coating composition. If the content is less than 10% by weight, the cross-linking density and hardness of the resin affects. If the content exceeds 80% by weight, the wear resistance is improved, but the film may be broken.

In addition, the said UV curable functional group containing binder resin can also use UV curable urethane (meth) acrylate type oligomer together.

The UV curable urethane (meth) acrylate-based oligomer is 10 to 60 parts by weight of an isocyanate prepolymer compound obtained by modifying a diisocyanate monomer having two isocyanate groups and a polycaprolactone modified hydroxy ethyl. It can manufacture by making 40-90 weight part of (meth) acrylates react.

The isocyanate prepolymer compound is triylene diisocyanate, naphthalene diisocyanate, diphenyl methane diisocyanate, xylene diisocyanate, hexamethylene diisocyanate, dicyclohexyl methane diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, lysine diisocyanate The compound which has two isocyanate groups in 1 molecule, such as an isocyanate and a novolak diisocyanate, can be obtained by denaturation by the method of isocyanurate modification, trimetholpropane (TMP) modification, biuret modification, etc.

The polycaprolactone modified hydroxy ethyl (meth) acrylate reacts with an isocyanate group and has a UV curable functional group (CH ₂ =).

The UV curable urethane (meth) acrylate-based oligomer is preferably included in the UV curable coating composition up to 10% by weight. When the content exceeds 10% by weight, the crosslinkability may increase, resulting in roughening of the surface of the coating film and cracking of the film.

The UV curable functional group-containing compound used in the present invention may be a polyfunctional or monofunctional monomer or oligomer having a meta (acryloyl) group copolymerizable with a UV curable functional group-containing binder resin in a molecule.

Specifically, as the monofunctional monomer having a meta (acryloyl) group in the molecule, 2-ethylhexyl acrylate, phenoxy ethyl acrylate, 2-ethoxy ethyl acrylate, 2-ethoxy ethoxy ethyl acrylate, 2 Hydroxy ethyl acrylate, 2-hydroxy propyl acrylate, polycaprolactone modified hydroxy ethyl acrylate, N-vinyl pyrrolidone, isobornyl acrylate, vinyl acetate, styrene, and the like. 1,6-hexanediol diacrylate, 1,4-butanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, propylene glycol diacrylate, dipropylene glycol diacrylate, and the like. As the functional monomer, 3 mol propyl of trimethylolpropane triacrylate, pentaerythritol triacrylate, and trimetholpropane Triacrylate of oxide adduct, triacrylate of 6 mole ethylene oxide adduct of trimetholpropane, glycerin propoxy triacrylate, dipentaerythritol hexaacrylate, hexaacrylate of caprolactone adduct of dipentaerythritol, and the like. The oligomers include unsaturated polyesters, polyester acrylates, polyether acrylates, acry acrylates, urethane acrylates, epoxy acrylates, and the like.

The UV curable functional group-containing compound is preferably contained in 1 to 30% by weight in the UV curable coating composition. When the content is less than 1% by weight, the coating film may not be formed cleanly, and when the content exceeds 30% by weight, the surface of the coating film may be rough.

The UV curable silicone graft or block copolymer used in the present invention is a compound having a UV curable functional group copolymerizable with a UV curable functional group-containing binder resin, and may be a graft copolymer or a block copolymer.

The UV curable silicone graft or block copolymer may be a vinyl monomer having a functional group such as graft type reactive silicone or block type reactive silicone, glycidyl group, isocyanate group, hydroxyl group, carboxyl group, or other copolymerizable with the reactive silicone. A vinyl monomer, a compound capable of reacting with the functional group of the vinyl monomer, and having a UV curable functional group may be used.

As the graft type reactive silicone, a compound represented by Chemical Formula 10 may be used.

[Formula 10]

Wherein n is an integer from 0 to 500.

As the block type reactive silicone, a compound represented by the following Formula 11 may be used.

[Formula 11]

Wherein m is an integer from 10 to 300 and l is an integer from 1 to 20.

As the vinyl monomer having a glycidyl group, glycidyl acrylate, glycidyl methacrylate, glycidyl allyl ether, etc. may be used, and as the vinyl monomer having an isocyanate group, 2-isocyanate ethyl (meth) acrylate , Methacryloyl isocyanate, vinyl isocyanate, etc. may be used, and as the vinyl monomer having a hydroxyl group, 2-hydroxy ethyl (meth) acrylate, hydroxy propyl (meth) acrylate, polyethylene glycol (meth) acrylate, Phenoxy hydroxy propyl acrylate may be used, and as the vinyl monomer having a carboxyl group, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, maleic anhydride, and the like may be used.

Other vinyl monomers copolymerizable with the reactive silicone include methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, t-butyl acrylate and octyl acryl. Latex, cyclohexyl acrylate, tetra hydroperryl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, cyclohexyl methacrylate Aliphatic acrylates or methacrylates such as stearyl methacrylate and lauryl methacrylate; Vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether; Nitrile-type monomers, such as styrene, such as styrene and (alpha) -methyl styrene, an acrylonitrile, methacrylonitrile; Fatty acid vinyls such as vinyl acetate and vinyl propionate; Halogen-containing monomers such as vinyl chloride, vinylidene chloride, vinyl fluoride and vinylidene fluoride; Olefins such as ethylene and propylene; Dienes such as isoprene, chloroprene, butadiene and the like can be used.

As the compound capable of reacting with the functional group of the vinyl monomer and having a UV curable functional group, the compound capable of reacting with a glycidyl group and having a UV curable functional group is acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, Maleic anhydride and the like can be used; 2-hydroxyethyl (meth) acrylate, hydroxy propyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, polystyrene glycol Compounds having an amino group such as alcohol type such as meth) acrylate, butoxy hydroxy acrylate and phenoxy acrylate can be used; 2-isocyanate ethyl (meth) acrylate, methacryloyl isocyanate, vinyl isocyanate and the like can be used as the compound which can react with a hydroxyl group and have a UV curable functional group; Glycidyl acrylate, glycidyl methacrylate, glycidyl allyl ether, etc. may be used as the compound capable of reacting with a carboxyl group and having a UV curable functional group.

The UV curable silicone graft or block copolymer is preferably included in 1 to 30% by weight in the UV curable coating composition. When the content is less than 1% by weight, the coating film may not be formed cleanly, and when the content exceeds 30% by weight, the surface of the coating film may be rough.

The fluorine-based compound used in the present invention serves to prevent contamination adhesion such as fingerprint traces and to easily remove the coating film of the present invention.

In particular, the fluorine-based compound contains a strong electronegativity fluorine that does not easily adhere to other materials on the surface, unlike the film coated with the conventional UV curable composition to increase the contact angle of the surface of the film coated with the coating composition of the present invention to prevent contamination Prevent, impart high hardness and scratch resistance, improve gloss and improve transparency. That is, by using the fluorine-based compound in the UV-curable coating composition of the present invention will be able to achieve the purpose of the present invention.

The fluorine-based compound should contain fluorine, and the type thereof is not particularly limited as long as it has a UV-curable functional group.

For example, an acrylate, methacrylate, vinyl or the like containing a perfluoro group may be used as the fluorine compound. At this time, the fluorine-based compound preferably has 1 to 6 UV curable functional groups. Specifically, the fluorine-based compound may be selected from compounds represented by the following Chemical Formulas 1 to 9, but the scope of the present invention is not limited thereto.

[Formula 1]

[Formula 2]

(3)

[Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In the formula 1 to 9,

X and Y are each independently F or CF ₃ ,

Z is H or CH ₃ ,

a, j, and m are each independently an integer of 1 to 16,

c, k and n are each independently an integer of 0 to 5,

b, d, e, f and g are each independently an integer from 0 to 200,

h and i are each independently an integer from 0 to 16,

이다.PFPE

to be.

The fluorine-based compound is preferably contained in 0.01 to 15% by weight in the UV curable coating composition. If the content is less than 0.01% by weight, the content of the fluorine-based compound having a strong electronegativity is low, which may cause a problem in improving fouling resistance. The hardness may be weakened, scratchability and transparency may be lowered. The effects of improving the stain resistance, hardness, scratch resistance and transparency are insignificant or deteriorated.

The photoinitiator used in the present invention is not particularly limited as long as it is a commonly used UV-curable initiator, specifically 1-hydroxy cyclohexylphenyl ketone, benzyl dimethyl ketal, hydroxydimethylacetophenone, benzoin, benzo Phosphorus methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether or mixtures thereof can be used. For example, the initiator represented by brand names Daracur 1173, Irgacure 184, and Irgacure 907 (above Ciba) can be used.

The photoinitiator is preferably included in 0.1 to 10% by weight in the UV curable coating composition. If the content is less than 0.1% by weight, curing may not occur, and if it exceeds 10% by weight, surface curing (Surface curing / through curing) may be severe.

In addition, solvents used in the present invention include benzene, toluene, methyl ethyl ketone, methyl isobutyl ketone, acetone, ethanol, tetrahydrofurfuryl alcohol, propyl alcohol, propylene carbonate, N-methyl pyrrolidinone, and N-vinyl pyrrolyl. Dinone, N-acetyl pyrrolidinone, N-hydroxy methyl pyrrolidinone, N-butyl pyrrolidinone, N-ethyl pyrrolidinone, N- (N-octyl) pyrrolidinone, N- (N-dodecyl Pyrrolidinone, 2-methoxyethyl ether, xylene, cyclohexane, 3-methyl cyclohexanone, ethyl acetate, butyl acetate, tetrahydrofuran, methanol, amyl propionate, methyl propionate, propylene glycol Methyl ether, diethylene glycol monobutyl ether, dimethyl sulfoxide, dimethyl formamide, ethylene glycol, hexafluoroantimonate, monoalkyl ether of ethylene glycol, dialkyl ether of ethylene glycol, two Cellosolve derivatives (cellosolve) or mixtures thereof.

The type and content of the solvent are preferably selected and used in consideration of physical properties such as coating film smoothness, erosion of the substrate by the solvent, adhesiveness, haze, pinhole phenomenon, and the like.

The UV-curable coating composition of the present invention comprising the above components is a negative electrode that does not easily adhere to other materials on the surface together with the UV-curable functional group-containing binder resin, UV-curable functional group-containing compound, UV-curable silicone graft or block copolymer By containing a large fluorine-based compound, unlike the film coated with the conventional UV curable composition, it is possible to prevent contamination by increasing the contact angle of the surface of the film coated with the coating composition of the present invention, and to provide high hardness and scratch resistance. The glossiness can be increased to improve transparency.

UV curable coating composition of the present invention as described above may be coated on a substrate. The UV curable coating composition may be applied to various substrates such as plastic, metal, glass, SiO ₂ film due to excellent adhesion to the substrate.

The coating composition may be coated on a substrate by a conventionally known coating method, for example, dip coating, spin coating, vapor deposition, two roll reverse coating, three roll reverse coating, gravure coating, It can be coated by a method such as micro gravure coating, die coating, curtain coating, bar coating, flow coating.

The film coated by the above method is preferably cured at a UV irradiation amount of 0.05 ~ 2J / ㎠ after drying, in particular, when cured in a nitrogen atmosphere can increase the surface curing degree can be improved pollution prevention and removal properties.

The coating composition is preferably coated with an ultra-thin coating thickness of 5nm ~ 1㎛ on the surface of the base material can maintain the hardness and optical properties of the base surface, and more preferably to a thickness of 8 ~ 100nm.

As described above, the coating film of the present invention coated with the UV curable coating composition may be applied without limitation as long as it is required for stain resistance and abrasion resistance, and may be formed by directly coating a component of a target device or formed on a substrate. It may be applied to the target device together with the later description.

The coating film according to the present invention is an anti-reflection layer (SiO ₂ ) of a liquid crystal display, a flat CRT surface such as a PC flat panel monitor, a notebook computer, a flat screen TV, an optical lens surface such as glasses, a camera, a lens for various measuring devices, a thermal head, an ink jet. Printer heads such as PDAs, PDAs, touch panel surfaces such as mobile phones, protective cover surfaces such as mobile phone windows, liquid crystal displays, organic light emitting displays (OLEDs), plasma displays and the like, but the scope of the present invention is not limited to these examples. .

Hereinafter, the present invention will be described in more detail with reference to examples. These embodiments are for purposes of illustration only and are not intended to limit the scope of protection of the present invention.

Example  One

80g of urethane acrylate EB1290 (manufactured by Cytec) as a UV-curable functional group-containing binder resin, 20g of 2-ethylhexyl acrylate as a UV-curable functional group-containing compound, 15g of ethyl acrylate as a UV-curable silicone graft or block copolymer, fluorine-based compound Wherein the compounds of Formula 1 (X and Y are each F, Z is CH ₃ , a, e and i are each 2, b, c, d, f and g are each 1, h is 3) 10 g, 5 g of Igacure 184 with a photoinitiator, 100 g of methyl ethyl ketone and 100 g of butyl acetate were mixed with a solvent and stirred for about 1 hour with a stirrer.

The prepared coating composition was spin-coated on the glass to have a curing thickness of 10 nm. Then, the coated film was dried in an oven at 60 ° C. for 5 minutes, and then irradiated with a polymerization mercury lamp to have a UV energy of 1 J / cm 2 to prepare a UV curable coating film.

Example  2

Phase 1 except for using the compound of Formula 2 (X is F, Z is CH ₃ , j is 4, k and n are each 2, m is 3) in Example 1 A coating film was prepared in the same manner as in Example 1.

Example  3

A coating film was prepared in the same manner as in Example 1, except that Optool DAC (produced by DAIKIN), a compound of Formula 3, was used as the fluorine compound in Example 1.

Example  4

In Example 1, the compound of Chemical Formula 4 (Z in Formula 4 is CH ₃ , X and Y in PFPE are each F, a, e and i are each 2, b, c, d, and f as the fluorine compound in Example 1). And g are each 1, and h is 3) to prepare a coating film in the same manner as in Example 1 above.

Example  5

In Example 1, the compound of Formula 5 (Z in Formula 9 is CH ₃ , X and Y are each F, and a, e, and i are 2, b, c, d, and f as the fluorine compound in Example 1, respectively. And g are each 1, and h is 3) to prepare a coating film in the same manner as in Example 1 above.

Example  6

10 g of a urethane (meth) acrylate-based oligomer obtained by reacting an isocyanate prepolymer compound obtained by isocyanurate-modified triylene diisocyanate with polycaprolactone-modified hydroxyethyl (meth) acrylate when preparing the coating composition in Example 1 A coating film was prepared in the same manner as in Example 1 except for further use.

Example  7

The coating composition prepared in Example 1 was dip coated onto a SiO ₂ film to have a curing thickness of 10 nm. Then, the coated film was dried in an oven at 60 ° C. for 5 minutes, and then irradiated with a polymerization mercury lamp to have a UV energy of 1 J / cm 2 to prepare a UV curable coating film.

Example  8

The coating composition prepared in Example 1 was dip coated onto a triacetyl cellulose film such that the curing thickness was 10 nm. Then, the coated film was dried in an oven at 60 ° C. for 5 minutes, and then irradiated with a polymerization mercury lamp to have a UV energy of 1 J / cm 2 to prepare a UV curable coating film.

Comparative example  One

A coating film was prepared in the same manner as in Example 1, except that the fluorine-based compound was not used in Example 1.

Comparative example  2

A coating film was prepared in the same manner as in Comparative Example 1, except that the composition of Comparative Example 1 was coated on the SiO ₂ film.

Comparative example  3

A coating film was prepared in the same manner as in Comparative Example 1, except that the composition of Comparative Example 1 was coated on the triacetyl cellulose film.

Using the coating films of Examples 1 to 8 and Comparative Examples 1 to 3 to evaluate the stain resistance, scratch resistance and film adhesion in the following manner, the results are shown in Table 1 below.

1. Pollution Resistance: The coating films were each stained with a black oil pen and wiped with Kimwipes after 10 seconds. This operation was repeated to evaluate the stain resistance by the number of times until the trace of the pen remained. At this time, evaluation was made into (circle) if the pen can be wiped 10 times or more, (triangle | delta) if it can wipe off a pen by 5-10 times, (triangle | delta), and if it can wipe off a pen by 1 to 5 times.

2. Abrasion resistance: 1 kg load was applied to the wearer on which steel batting # 0000 was installed, and the presence or absence of scratches was visually evaluated.

3. Adhesiveness of the film: A cross cut nichiban tape peel test was performed on the coated film. Specifically, by making 11 horizontal and vertical scales of 1 mm each to the substrate at 1 mm intervals on the coating film, 100 eyes of 1 mm2 were made, and a cellophane tape was attached and sharply removed three times in one place. The result was measured.

○: cross-linking curing even if repeated three times

(Triangle | delta): When repeating 3 times and the number of peeling eyes is 1-50

X: 3 times repeated peeling eyes 51 to 100

division

Pollution resistance
Wear resistance
Adhesiveness of membrane
Example 1

○
Good
○
Example 2

○
Good
○
Example 3

○
Good
○
Example 4

○
Good
○
Example 5

○
Good
○
Example 6

○
Good
○
Example 7

○
Good

○
Example 8

○
Good

○
Comparative Example 1

△
Bad
△
Comparative Example 2

×
Bad
△
Comparative Example 3

×
Bad
△

As shown in Table 1, the coating film coated with the composition of Examples 1 to 6 containing the fluorine-based compound according to the present invention, compared with Comparative Example 1 containing no fluorine-based compound, stain resistance, wear resistance and adhesion of the membrane This excellence could be confirmed. In particular, the coating film coated with the composition of Example 6 further using a urethane (meth) acrylate-based oligomer showed better wear resistance than Examples 1 to 5.

In addition, the coating composition including the fluorine-based compound of the present invention exhibited excellent stain resistance, abrasion resistance, and adhesion even when coated on not only glass, but also SiO ₂ film and plastic. It can be applied to various substrates such as glass, SiO ₂ film, etc., so that it can be applied to anti-reflection layer (SiO ₂ ) of LCD, flat CRT surface of PC, flat screen monitor, notebook, flat screen TV, glasses, camera, lens of various measuring instruments, etc. It can be expected to be applied to a lens surface, a thermal head, a printer head such as an inkjet, a touch panel surface of a PDA, a mobile phone, a protective cover surface of a mobile phone window, a liquid crystal display, an organic light emitting display (OLED), a plasma display, and the like.

Although the present invention has been described as the preferred embodiment mentioned above, it is possible to make various modifications or variations without departing from the spirit and scope of the invention. The appended claims also cover such modifications and variations as fall within the spirit of the invention.

Claims (16)

delete 10 to 80% by weight of UV-curable functional group-containing binder resin; 1-30 weight% of UV-curable functional group containing compounds; 1-30% by weight of UV curable silicone graft or block copolymer; 0.01-15 wt% of fluorine-based compounds; 0.1-10% by weight of photoinitiator; And Solvent residue; UV curable coating composition comprising a. delete 3. The method of claim 2, The UV curable functional group-containing binder resin may be used with an isocyanate prepolymer compound and an isocyanate prepolymer compound obtained by reacting a polycaprolactone-modified hydroxyethyl (meth) acrylate. . delete delete delete delete delete delete delete delete delete delete delete delete