Curable composition and coating layer

Abstract

The present invention relates to a curable composition and a coating layer comprising the curable composition, the composition being capable of easily forming a coating layer having excellent dispersion stability and improved mechanical properties, chemical resistance and optical properties.

Description

Curable composition and coating layer

[0001] The present invention relates to a curable composition and a coating layer comprising a cured product thereof.

[0002] Recently, design aspects have become important factors alongside functionality for glass and plastic substrates used in displays and industrial interior and exterior materials. Accordingly, active research is being conducted on coating materials that simultaneously achieve both functional and design aspects by adding pigments and dyes to functional coating compositions. There is a growing need for functional coating liquid materials containing pigments and dyes to meet the specific functions and characteristics required by various industries, such as eyeglass lenses, camera lenses, automotive interiors, shatterproof films, decorative films, and display color correction films.

[0003] The present invention provides a curable composition capable of easily realizing a coating layer having excellent dispersion stability and improved mechanical properties, chemical resistance, and optical properties, and a coating layer comprising a cured product thereof.

[0004] However, the problems that the present invention aims to solve are not limited to those mentioned above, and other unmentioned problems will be clearly understood by those skilled in the art from the description below.

[0005] One embodiment of the present invention provides a curable composition comprising: a silicone sol containing one or more first functional groups including a hydroxyl group and one or more second functional groups including a reactive functional group other than a hydroxyl group; and an initiator.

[0006] According to one embodiment of the present invention, the ratio of the first functional group to the second functional group in the silicon sol may be 1:9 to 9:1.

[0007] According to one embodiment of the present invention, the ratio of the first functional group to the second functional group in the silicon sol may exceed 1.

[0008] According to one embodiment of the present invention, the second functional group may include at least one reactive functional group among an amino group, a (meth)acrylate group, a vinyl group, an epoxy group, and a thiol group.

[0009] According to one embodiment of the present invention, the second functional group may further include at least one non-reactive functional group among a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms and an aromatic group having 6 to 30 carbon atoms.

[0010] According to one embodiment of the present invention, the curable composition further comprises a coloring agent, and the ratio of the size of the sol particles included in the silicone sol to the size of the coloring agent may be 1:0.01 to 1:5.

[0011] According to one embodiment of the present invention, the content of the silicone sol may be 80 parts by weight or more based on 100 parts by weight of the solid content of the curable composition.

[0012] According to one embodiment of the present invention, based on 100 parts by weight of solid content of the curable composition, the content of the initiator may be 0.1 parts by weight or more and 20 parts by weight or less.

[0013] According to one embodiment of the present invention, the curable composition further comprises a coloring agent, and based on 100 parts by weight of the solid content of the curable composition, the content of the coloring agent may be 0.1 parts by weight or more and 10 parts by weight or less.

[0014] One embodiment of the present invention provides a coating layer comprising a cured product of the curable composition.

[0015] A curable composition according to one embodiment of the present invention may have excellent dispersion stability.

[0016] In addition, the curable composition according to one embodiment of the present invention can effectively realize a coating layer having excellent adhesion, chemical resistance, and optical properties.

[0017] In addition, the coating layer according to one embodiment of the present invention can easily achieve excellent dispersibility, adhesion, chemical resistance, and optical properties by including a cured product of the curable composition.

[0018] The effects of the present invention are not limited to those described above, and unmentioned effects will be clearly understood by those skilled in the art from the present specification and the accompanying drawings.

[0019] Throughout this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0020] Throughout this specification, when a component is described as being located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0021] Throughout the entire specification, the unit "parts by weight" may refer to the ratio of weight between each component.

[0022] Throughout this specification, terms including ordinal numbers, such as “first” and “second,” are used for the purpose of distinguishing one component from another and are not limited by said ordinal numbers. For example, within the scope of the invention, the first component may also be named the second component, and similarly, the second component may be named the first component.

[0023] Throughout this specification, "(meth)acrylate" is used to refer collectively to acrylates and methacrylates.

[0024] Throughout the entire specification, "at least one of a, b and c" may include a, b, or c alone, or two or more combinations selected from the group consisting of a, b, and c.

[0025] Throughout this specification, silicon sol may mean a colloidal solution in which silicon particles are dispersed in a sol form or a solution in which silicon particles are dissolved in a sol form.

[0026]

[0027] The present specification will be described in more detail below.

[0028] One embodiment of the present invention provides a curable composition comprising: a silicone sol containing one or more first functional groups including a hydroxyl group and one or more second functional groups including a reactive functional group other than a hydroxyl group; and an initiator.

[0029] A curable composition according to one embodiment of the present invention may have excellent dispersion stability. In addition, the curable composition can effectively realize a coating layer having excellent adhesion, chemical resistance, and optical properties.

[0030] According to one embodiment of the present invention, the silicone sol may include a first functional group and a second functional group. The first functional group may refer to a functional group group comprising one or more hydroxyl groups. Specifically, the first functional group may be a hydroxyl group group comprising one or more hydroxyl groups. Through the hydroxyl groups included in the first functional group of the silicone sol, the adhesion of the curable composition to a substrate may be improved. Specifically, the hydroxyl group contained in the silicone sol can form covalent bonds with Si-OH and Si-O present on the surface of the substrate, thereby effectively increasing the bonding and adhesion of the curable composition to glass during coating. At this time, the substrate may be glass or a plastic film. At this time, the plastic film may include polyethylene terephthalate (PET) film, polyvinyl chloride (PVC) film, polyethylene (PE) film, etc., but the type of plastic film is not limited thereto. A coating layer comprising a cured product of the above-mentioned curable composition can be provided on the surface of the above-mentioned substrate and utilized as a protective coating layer, a decoration coating layer, etc.

[0031] According to one embodiment of the present invention, the second functional group may include one or more reactive functional groups other than a hydroxyl group. The reactive functional group may induce a curing reaction by the initiator. Through the reactive functional group included in the second functional group of the silicone sol, the curable composition can stably form a coating layer.

[0032] According to one embodiment of the present invention, the ratio of the first functional group to the second functional group in the silicone sol may be 1:9 to 9:1. That is, the ratio of the first functional group to the second functional group may be 1 to 9:9 to 1. Specifically, the ratio of the first functional group to the second functional group may be 1:9 to 1:1, and the ratio of the first functional group to the second functional group may be 9:1 to 1:1. More specifically, the ratio of the first functional group to the second functional group may be 1:9 to 1:1, 2:8 to 1:1, 3:7 to 1:1, 4:6 to 1:1, 9:1 to 1:1, 8:2 to 1:1, 7:3 to 1:1, or 6:4 to 1:1. When the ratio of the first functional group and the second functional group is within the aforementioned range, the adhesion of the curable composition to glass can be improved. In addition, the curable composition can effectively realize a coating layer having excellent adhesion, chemical resistance, and optical properties.

[0033] At this time, the ratio of the first functional group to the second functional group may refer to the molar ratio of the first functional group to the second functional group. The ratio of the first functional group to the second functional group contained in the silicon sol can be calculated through 1H nuclear magnetic resonance spectroscopy. Specifically, the area of ​​the peaks representing the first functional group and the second functional group in the NMR analysis results of the silicon sol can be calculated through integration, and the ratio of the first functional group to the second functional group can be obtained using the calculated area.

[0034] According to one embodiment of the present invention, the ratio of the first functional group to the second functional group in the silicone sol may exceed 1. That is, the “first functional group / second functional group” may exceed 1. Specifically, the ratio of the first functional group to the second functional group may be 9 to 1.1:1, 8 to 1.1:1, 7 to 1.1:1, 6 to 1.1:1, 5 to 1.1:1, 4 to 1.1:1, 3 to 1.1:1, or 2 to 1.1:1. In addition, the ratio calculated as “first functional group / second functional group” may be 1.1 or more and 9 or less, 1.1 or more and 8 or less, 1.1 or more and 7 or less, 1.1 or more and 6 or less, 1.1 or more and 5 or less, 1.1 or more and 4 or less, 1.1 or more and 3 or less, or 1.1 or more and 2 or less. By using the silicone sol in which the ratio of the first functional group to the second functional group exceeds 1, the curable composition can effectively realize a coating layer having excellent adhesion, chemical resistance, and optical properties.

[0035] According to one embodiment of the present invention, the second functional group may include at least one reactive functional group selected from an amino group, a (meth)acrylate group, a vinyl group, an epoxy group, and a thiol group. Specifically, the second functional group may include at least one selected from a (meth)acrylate group and an epoxy group. The curable composition containing the aforementioned reactive functional group can stably form a coating layer, and the formed coating layer can easily achieve excellent adhesion, chemical resistance, and optical properties.

[0036] According to one embodiment of the present invention, the second functional group may include at least one non-reactive functional group among a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms and an aromatic group having 6 to 30 carbon atoms. Specifically, the alkyl group may be straight-chain, and the number of contained carbon atoms may be 1 to 8, 1 to 6, 1 to 4, or 1 to 2. Additionally, the aromatic group may be a phenyl group. When the silicone sol includes the non-reactive functional group, the curable composition can effectively provide a coating layer with improved mechanical properties, such as hardness.

[0037] According to one embodiment of the present invention, the ratio of the reactive functional group to the non-reactive functional group included in the second functional group may be 1:9 to 9:1. That is, the ratio of the reactive functional group to the non-reactive functional group may be 1 to 9:9 to 1. Specifically, the ratio of the reactive functional group to the non-reactive functional group may be 1:9 to 1:1, and the ratio of the reactive functional group to the non-reactive functional group may be 9:1 to 1:1. Specifically, the ratio of the reactive functional group to the non-reactive functional group may be 1:9 to 1:1, 2:8 to 1:1, 3:7 to 1:1, 4:6 to 1:1, 9:1 to 1:1, 8:2 to 1:1, 7:3 to 1:1, or 6:4 to 1:1. When the ratio of the reactive functional group to the non-reactive functional group is within the aforementioned range, the curable composition can effectively realize a coating layer having excellent hardness, adhesion, chemical resistance, and optical properties.

[0038] According to one embodiment of the present invention, the ratio of a reactive functional group to a non-reactive functional group included in the second functional group may exceed 1 in the silicone sol. That is, the “reactive functional group / non-reactive functional group” included in the second functional group may exceed 1. Specifically, the ratio of the reactive functional group to the non-reactive functional group may be 9 to 1.1:1, 8 to 1.1:1, 7 to 1.1:1, 6 to 1.1:1, 5 to 1.1:1, 4 to 1.1:1, 3 to 1.1:1, or 2 to 1.1:1. In addition, the ratio calculated as “reactive functional group / non-reactive functional group” may be 1.1 or more and 9 or less, 1.1 or more and 8 or less, 1.1 or more and 7 or less, 1.1 or more and 6 or less, 1.1 or more and 5 or less, 1.1 or more and 4 or less, 1.1 or more and 3 or less, or 1.1 or more and 2 or less. By using the silicone sol in which the ratio of the reactive functional group to the non-reactive functional group included in the second functional group exceeds 1, the curable composition can effectively realize a coating layer having superior adhesion, chemical resistance, and optical properties.

[0039] According to one embodiment of the present invention, the curable composition may further include a coloring agent. The coloring agent may be any pigment, dye, etc. used in the art without limitation. The coloring agent is a colorant that produces a desired color, and may be used without limitation as long as it is capable of producing a color in the visible light range. For example, the coloring agent may include at least one of anthraquinone compounds, squaryllium compounds, cyanine compounds, phthalocyanine compounds, thiophene compounds, diimmonium compounds, and cobalt compounds. However, the type of coloring agent is not limited.

[0040] According to one embodiment of the present invention, the ratio of the size of the sol particles included in the silicone sol to the size of the coloring agent may be 1:0.01 to 1:5. Specifically, the ratio of the size of the sol particles included in the silicone sol to the size of the colorant is 1:0.05 to 1:4.7, 1:0.09 to 1:4.4, 1:0.1 to 1:4, 1:0.5 to 1:3.7, 1:1 to 1:3.3, 1:1.3 to 1:3, 1:1.7 to 1:2.8, 1:2 to 1:2.4, 1:0.1 to 1:5, 1:0.3 to 1:5, 1:0.5 to 1:5, 1:0.8 to 1:4.5, 1:1 to 1:4, 1:1.5 to 1:3.5, 1:2 to 1:3, 1:0.5 to 1:3, 1:0.7 to 1:2.8, 1:1.1 to It may be 1:2.5, 1:1.3 to 1:2.3, 1:1.6 to 1:2, 1:2.5 to 1:5, 1:2.7 to 1:4.8, 1:2.9 to 1:4.5, 1:3.2 to 1:4.2, or 1:3.5 to 1:4. When the ratio of the size of the sol particles included in the silicone sol to the size of the colorant is within the aforementioned range, the colorant can be dispersed more homogeneously and stably in the curable composition. Furthermore, by adjusting the ratio of the size of the sol particles included in the silicone sol to the aforementioned range, the curable composition can easily realize a coating layer having improved optical properties.

[0041] According to one embodiment of the present invention, the size of the coloring agent may be 0.2 nm or more and 100 μm or less, 0.5 nm or more and 80 μm or less, 0.8 nm or more and 60 μm or less, 1 nm or more and 40 μm or less, 5 nm or more and 20 μm or less, 10 nm or more and 10 μm or less, 30 nm or more and 1 μm or less, 0.2 nm or more and 10 μm or less, 1 nm or more and 5 μm or less, 10 nm or more and 3 μm or less, 50 nm or more and 1 μm or less, 100 nm or more and 800 nm or less, 300 nm or more and 500 nm or less, 0.2 nm or more and 500 nm or less, 1 nm or more and 300 nm or less, 5 nm or more and 150 nm or less, 10 nm or more and 100 nm or less, or 20 nm or more and 50 nm or less. Meanwhile, the size of the colorant is not limited to this, and depending on the application in which the curable composition is used, colorants of various sizes outside the aforementioned range may be used.

[0042] According to one embodiment of the present invention, the size of the sol particles included in the silicone sol can be varied depending on the size of the coloring agent included in the curable composition. Specifically, the size of the sol particles included in the silicone sol may satisfy the aforementioned range in the ratio of the size of the sol particles included in the silicone sol to the size of the coloring agent.

[0043] According to one embodiment of the present invention, the content of the silicone sol may be 80 parts by weight or more based on 100 parts by weight of the solid content of the curable composition. Specifically, the solid content of the silicone sol may be 80 parts by weight or more based on 100 parts by weight of the solid content of the curable composition. Specifically, the content of the silicone sol is, based on 100 parts by weight of the solid content of the curable composition, 80 parts by weight or more and 99.9 parts by weight or less, 81 parts by weight or more and 99.7 parts by weight or less, 82 parts by weight or more and 99.5 parts by weight or less, 83 parts by weight or more and 99 parts by weight or less, 85 parts by weight or more and 98 parts by weight or less, 87 parts by weight or more and 96 parts by weight or less, 89 parts by weight or more and 95 parts by weight or less, 90 parts by weight or more and 93 parts by weight or less, 91 parts by weight or more and 92 parts by weight or less, 80 parts by weight or more and 95 parts by weight or less, 82.5 parts by weight or more and 92.5 parts by weight or less, 85 parts by weight or more and 90 parts by weight or less, 86 parts by weight or more and 88 parts by weight or less, 90 parts by weight or more and 99.7 parts by weight or less, 91.5 parts by weight or more and 99 parts by weight or less, and 93 parts by weight or more and 98.5 parts by weight or less. The amount may be 94.5 parts by weight or more and 96 parts by weight or less. In this case, the content of the silicon sol may refer to the content of silicon sol particles, which are the solids contained in the silicon sol. When the content of the silicon sol is within the aforementioned range, the curable composition can achieve excellent dispersion stability. Furthermore, the curable composition can effectively form a coating layer having excellent adhesion, chemical resistance, and optical properties.

[0044] According to one embodiment of the present invention, the curable composition comprises an initiator, and any initiator used in the art may be used without limitation. For example, the initiator may include at least one of a radical initiator, a cationic photoinitiator, a cationic thermal initiator, and an amine-based initiator.

[0045] Specifically, the radical initiator may include at least one of a photoradical initiator and a thermal radical initiator. The above photoradical initiators are trichloroacetophenone, diethoxyacetophenone, 1-phenyl-2-hydroxyl-2-methylpropane-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1-one, 2,4,6-trimethyl benzoyl diphenylphosphine oxide, camphor quinine, 2,2'-azobis(2-methylbutyronitrile), dimethyl-2,2'-azobis(2-methyl butylate), It may include at least one of 3,3-dimethyl-4-methoxy-benzophenone, p-methoxybenzophenone, 2,2-diethoxyacetophenone, and 2,2-dimethoxy-1,2-diphenyl ethane-1-one. The thermal radical initiator may include at least one of t-butylperoxymaleic acid, t-butylhydroperoxide, 2,4-dichlorobenzoylperoxide, 1,1-di(t-butylperoxy)-3,3,5-trimethylcyclohexane, and N-butyl-4,4'-di(t-butylperoxy)valerate.

[0046] In addition, cationic photoinitiators include sulfonium-based compounds such as triphenylsulfonium and diphenyl-4-(phenylthio)phenylsulfonium, iodium compounds such as diphenyliodonium or bis(dodecylphenyl)iodonium, diazonium compounds such as phenyldiazonium, ammonium compounds such as 1-benzyl-2-cyanopyrinium or 1-(naphthylmethyl)-2-cyanopridinium, (4-methylphenyl)[4-(2-methylpropyl)phenyl]-hexafluorophosphate iodonium, bis(4-t-butylphenyl)hexafluorophosphate iodonium, diphenylhexafluorophosphate iodonium, diphenyltrifluoromethanesulfonate iodonium, triphenylsulfonium tetrafluoroborate, tri-p-toylsulfonium hexafluorophosphate, tri-p-toylsulfonium trifluoromethanesulfonate, and Fe cations such as (2,4-cyclopentadiene-1-yl)[(1-methylethyl)benzene]-Fe and BF4 - , PF6 - , SbF6 - [BQ4]-onium salt combinations such as the above may be used (wherein Q is a phenyl group substituted with at least two fluorine or trifluoromethyl groups).

[0047] In addition, cationic thermal initiators such as triphosphates, boron trifluoride ether complexes, boron trifluoride, etc., cationic or proton acid catalysts, various onium salts such as ammonium salts, phosphonium salts, and sulfonium salts, and methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, phenyltriphenylphosphonium bromide, etc., may be used without limitation, and these initiators may also be added in various mixed forms, and may be mixed with the various radical initiators specified above.

[0048] In addition, amine-based initiators such as ethylenediamine, triethylenetetramine, tetraethylenepentamine, 1,3-diaminopropane, dipropylentiamine, 3-(2-aminoethyl)amino-propylamine, N,N'-bis(3-aminopropyl)-ethylenediamine, 4,9-dioxadodecane-1,12-diamine, 4,7,10-trioxatridecane-1,13-diamine, hexamethylenediamine, 2-methylpentamethylenediamine, 1,3-bisaminomethylcyclohexane, bis(4-animocyclohexyl)methane, norbornendiamine, 1,2-diaminocyclohexane, etc. may be used.

[0049] According to one embodiment of the present invention, based on 100 parts by weight of solid content of the curable composition, the content of the initiator may be 0.1 parts by weight or more and 20 parts by weight or less. Specifically, the content of the initiator is, based on 100 parts by weight of the solid content of the curable composition, 0.3 parts by weight or more and 19 parts by weight or less, 0.5 parts by weight or more and 17.5 parts by weight or less, 1 part by weight or more and 15 parts by weight or less, 3 parts by weight or more and 12.5 parts by weight or less, 4.5 parts by weight or more and 11 parts by weight or less, 5.5 parts by weight or more and 10 parts by weight or less, 7 parts by weight or more and 8.5 parts by weight or less, 0.1 parts by weight or more and 10 parts by weight or less, 0.4 parts by weight or more and 9 parts by weight or less, 0.8 parts by weight or more and 8 parts by weight or less, 1 part by weight or more and 7 parts by weight or less, 2 parts by weight or more and 6 parts by weight or less, 3.5 parts by weight or more and 5.5 parts by weight or less, 10 parts by weight or more and 20 parts by weight or less, 10.5 parts by weight or more and 18 parts by weight or less, 11 parts by weight or more and 16 parts by weight or less, or 12.5 parts by weight The amount may be 14.5 parts by weight or less. When the content of the initiator is within the aforementioned range, the curable composition can be cured stably, thereby effectively forming a coating layer.

[0050] According to one embodiment of the present invention, the curable composition further comprises a coloring agent, and based on 100 parts by weight of the solid content of the curable composition, the content of the coloring agent may be 0.1 parts by weight or more and 10 parts by weight or less. Specifically, the content of the coloring agent may be 0.3 parts by weight or more and 9.5 parts by weight or less, 0.5 parts by weight or more and 9 parts by weight or less, 1 part by weight or more and 9 parts by weight or less, 3 parts by weight or more and 8.5 parts by weight or less, 4 parts by weight or more and 7 parts by weight or less, 4.5 parts by weight or more and 6 parts by weight or less, 0.1 parts by weight or more and 7.5 parts by weight or less, 0.3 parts by weight or more and 7 parts by weight or less, 0.6 parts by weight or more and 6.5 parts by weight or less, 1 part by weight or more and 5.5 parts by weight or less, 1.3 parts by weight or more and 5 parts by weight or less, 1.8 parts by weight or more and 4.5 parts by weight or less, 5 parts by weight or more and 10 parts by weight or less, 6 parts by weight or more and 9 parts by weight or less, or 7 parts by weight or more and 8 parts by weight or less, based on 100 parts by weight of the solid content of the curable composition. When the content of the above-mentioned coloring agent is within the aforementioned range, the coloring agent can be stably and evenly dispersed within the curable composition. Furthermore, the curable composition can easily form a coating layer having a desired color.

[0051] According to one embodiment of the present invention, the curable composition may include an additive. In this case, the additive used in the art may be used without limitation. Specifically, the curable composition may include an additive for surface planarization of the coating layer. The surface planarization additive may include at least one of a silicone-based additive and an acrylic-based additive. The silicone-based additive may include at least one of BYK-300, BYK-301, BYK-302, BYK-331, BYK-335, BYK-306, BYK-330, BYK-341, BYK-344, BYK-307, BYK-333, and BYK-310, but is not limited thereto. The acrylic additive may include at least one of BYK-340, BYK-350, BYK-352, BYK-354, BYK-355, BYK-356, BYK-358N, BYK-359, BYK-361N, BYK-380N, BYK-381, BYK-388, BYK-390, BYK-392, BYK-394, and BYK-399, but is not limited thereto. By using the surface planarization additive, the surface planarity of the coating layer being manufactured can be further improved.

[0052] According to one embodiment of the present invention, the curable composition may include a solvent. The solvent may be any solvent used in the art without limitation. Specifically, various solvents may be used, but are not limited to, alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, butyl alcohol, and cellosolve-based solvents, ketones such as lactate-based solvents, acetone, and methyl(isobutyl)ethyl ketone, glycols such as ethylene glycol, furans such as tetrahydrofuran, and polar solvents such as dimethylformamide, dimethylacetamide, and N-methyl-2-pyrrolidone, as well as hexane, cyclohexane, cyclohexanone, toluene, xylene, cresol, chloroform, dichlorobenzene, dimethylbenzene, trimethylbenzene, pyridine, methylnaphthalene, nitromethane, acrylonitrile, methylene chloride, octadecylamine, aniline, dimethyl sulfoxide, and benzyl alcohol.

[0053] According to one embodiment of the present invention, the curable composition may include a curing accelerator, and any curing accelerator used in the art may be used without limitation. For example, the above curing accelerator is a triazine compound such as acetoguanamin, benzoguanamine, 2,4-diamino-6-vinyl-s-triazine, an imidazole compound such as imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, vinylimidazole, 1-methylimidazole, 1,5-diazabicyclo[4.3.0]nonen-5,1,8-diazabicyclo[5.4.0]undecen-7, triphenylphosphine, diphenyl(p-tril)phosphine, tris(alkylphenyl)phosphine, tris(alkoxyphenyl)phosphine, ethyltriphenylphosphonium phosphate, tetrabutylphosphonium hydroxide, tetrabutylphosphonium acetate, tetrabutylphosphonium hydrogendifluoride, Tetrabutylphosphonium dihydrogentrifluoride, etc. may also be used. Furthermore, phthalic anhydride, trimellitic anhydride, pyrromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl anhydride, hydrogenated methyl anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 2,4-diethylglutaric anhydride, etc. may also be used as curing accelerators.

[0054]

[0055] One embodiment of the present invention provides a coating layer comprising a cured product of the curable composition.

[0056] A coating layer according to one embodiment of the present invention can easily achieve excellent dispersibility, adhesion, chemical resistance, and optical properties by including a cured product of the curable composition.

[0057] According to one embodiment of the present invention, the coating layer can be used for purposes such as eyeglass lenses, camera lenses, automotive interior materials, shatterproof films, decoration films, and display color correction films.

[0058] According to one embodiment of the present invention, the thickness of the coating layer may be 10 nm or more and 100 μm or less. Meanwhile, it is obvious that a coating layer with a thickness outside the aforementioned range may be provided depending on the application in which the coating layer is utilized.

[0059]

[0060] Hereinafter, the present invention will be described in detail with reference to examples to specifically explain the invention. However, the embodiments according to the present invention may be modified in various different forms, and the scope of the present invention is not to be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present invention to those with average knowledge in the art.

[0061]

[0062] Preparation of silicon sol

[0063] Example 1-1

[0064] 300 g of distilled water, 10 g of ethanol, 190 g of methanol, and 10 g of a 1 wt% aqueous solution of formic acid were added dropwise to a dry flask equipped with a condenser and a stirrer, and the temperature of the flask was fixed at 3 ℃ and stirred for 1 hour. 10.4 g (0.05 mol) of TEOS (Tetraethyl orthosilicate) and 224.5 g (0.95 mol) of 3-GPTMS (3-Glycidoxypropyl trimethoxysilane) were added dropwise, and the temperature was raised to 25 ℃ and stirred for an additional 6 hours to complete the reaction.

[0065] Dynamic light scattering particle size analysis of the reaction-completed mixture confirmed that silicon sol containing sol particles with an average size of about 25 nm was produced. In addition, 1H nuclear magnetic resonance spectroscopy confirmed that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 1:9.

[0066]

[0067] Examples 1-2

[0068] A silicon sol was prepared in the same manner as in Example 1-1, except that 20 g of ethanol, 180 g of methanol, 20.8 g (0.1 mol) of TEOS, and 212.7 g (0.9 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0069] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 2:8.

[0070]

[0071] Examples 1-3

[0072] A silicon sol was prepared in the same manner as in Example 1-1, except that 40 g of ethanol, 160 g of methanol, 41.7 g (0.2 mol) of TEOS, and 198.0 g (0.8 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0073] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 3:7.

[0074]

[0075] Examples 1-4

[0076] A silicon sol was prepared in the same manner as in Example 1-1, except that 50 g of ethanol, 150 g of methanol, 52.1 g (0.25 mol) of TEOS, and 177.2 g (0.75 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0077] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 4:6.

[0078]

[0079] Examples 1-5

[0080] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, and 141.8 g (0.6 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0081] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 5:5.

[0082]

[0083] Examples 1-6

[0084] A silicon sol was prepared in the same manner as in Example 1-1, except that 90 g of ethanol, 110 g of methanol, 93.7 g (0.45 mol) of TEOS, and 130.0 g (0.55 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0085] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 6:4.

[0086]

[0087] Examples 1-7

[0088] A silicon sol was prepared in the same manner as in Example 1-1, except that 100 g of ethanol, 100 g of methanol, 104.2 g (0.5 mol) of TEOS, and 118.2 g (0.5 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0089] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 7:3.

[0090]

[0091] Examples 1-8

[0092] A silicon sol was prepared in the same manner as in Example 1-1, except that 120 g of ethanol, 80 g of methanol, 125.0 g (0.6 mol) of TEOS, and 94.5 g (0.4 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0093] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 8:2.

[0094]

[0095] Examples 1-9

[0096] A silicon sol was prepared in the same manner as in Example 1-1, except that 160 g of ethanol, 40 g of methanol, 166.6 g (0.8 mol) of TEOS, and 47.3 g (0.2 mol) of 3-GPTMS were used, in comparison to Example 1-1.

[0097] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to glycidyl groups (epoxy groups) contained in the silicon sol was 9:1.

[0098]

[0099] Examples 1-10

[0100] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol was used instead of 10 g of ethanol, 120 g of methanol instead of 190 g of methanol, 83.3 g (0.4 mol) of TEOS instead of 10.4 g (0.05 mol) of TEOS, and 140.6 g (0.6 mol) of 3-acryloyloxypropyltrimethoxysilane instead of 224.5 g (0.95 mol) of 3-GPTMS.

[0101] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to acrylic groups contained in the silicon sol was 5:5.

[0102]

[0103] Example 1-11

[0104] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 127.6 g (0.54 mol) of 3-GPTMS, and 8.2 g (0.06 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0105] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:4.5:0.5.

[0106]

[0107] Examples 1-12

[0108] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 113.4 g (0.48 mol) of 3-GPTMS, and 16.3 g (0.12 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0109] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:4:1.

[0110]

[0111] Examples 1-13

[0112] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 99.2 g (0.42 mol) of 3-GPTMS, and 24.5 g (0.18 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0113] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:3.5:1.5.

[0114]

[0115] Examples 1-14

[0116] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 85.1 g (0.36 mol) of 3-GPTMS, and 32.7 g (0.24 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0117] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:3:2.

[0118]

[0119] Examples 1-15

[0120] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 70.9 g (0.3 mol) of 3-GPTMS, and 40.9 g (0.3 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0121] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:2.5:2.5.

[0122]

[0123] Examples 1-16

[0124] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 56.7 g (0.24 mol) of 3-GPTMS, and 49 g (0.36 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0125] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:2:3.

[0126]

[0127] Examples 1-17

[0128] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 42.5 g (0.18 mol) of 3-GPTMS, and 57.2 g (0.42 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0129] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:1.5:3.5.

[0130]

[0131] Examples 1-18

[0132] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 28.4 g (0.12 mol) of 3-GPTMS, and 65.4 g (0.48 mol) of methyl tirmethoxysilane were used, in comparison to Example 1-1.

[0133] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:1:4.

[0134]

[0135] Examples 1-19

[0136] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol, 120 g of methanol, 83.3 g (0.4 mol) of TEOS, 14.2 g (0.06 mol) of 3-GPTMS, and 73.5 g (0.54 mol) of methyl tirmethoxysilane were used, in contrast to Example 1-1.

[0137] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups, glycidyl groups (epoxy groups), and methyl groups contained in the silicon sol was 5:0.5:4.5.

[0138] (1) First functional group Second functional group (1):(2):(3)(2) Reactive functional group (3) Non-reactive functional group Example 1-1 Hydroxyl glycidyl group-1:9:0 Example 1-2 Hydroxyl glycidyl group-2:8:0 Example 1-3 Hydroxyl glycidyl group-3:7:0 Example 1-4 Hydroxyl glycidyl group-4:6:0 Example 1-5 Hydroxyl glycidyl group-5:5:0 Example 1-6 Hydroxyl glycidyl group-6:4:0 Example 1-7 Hydroxyl glycidyl group-7:3:0 Example 1-8 Hydroxyl glycidyl group-8:2:0 Example 1-9 Hydroxyl glycidyl group-9:1:0 Example 1-10 Hydroxyl acrylic group 5:5:0 Example 1-11 Hydroxyl glycidyl methyl group 5:4.5:0.5 Example 1-12 Hydroxyl glycidyl methyl group 5:4:1 Example 1-13 Hydroxyl glycidyl methyl group 5:3.5:1.5 Example 1-14 Hydroxyl glycidyl methyl group 5:3:2 Example 1-15 Hydroxyl glycidyl methyl group 5:2.5:2.5 Example 1-16 Hydroxyl glycidyl methyl group 5:2:3 Example 1-17 Hydroxyl glycidyl methyl group 5:1.5:3.5 Example 1-18 Hydroxyl glycidyl methyl group 5:1:4 Example 1-19 Hydroxyl glycidyl methyl group 5:0.5:4.5

[0139]

[0140] Comparative Example 1-1

[0141] 300 g of distilled water, 200 g of ethanol, and 10 g of a 1 wt% aqueous solution of formic acid were added dropwise to a dry flask equipped with a condenser and a stirrer, and the temperature of the flask was fixed at 3 ℃ and stirred for 1 hour. 208.3 g (1.0 mol) of TEOS (Tetraethyl orthosilicate) was added dropwise, the temperature was raised to 25 ℃, and the reaction was completed after stirring for an additional 6 hours.

[0142] Dynamic light scattering particle size analysis of the reaction-completed mixture confirmed that silicon sol containing sol particles with an average size of about 25 nm was produced. In addition, the presence of hydroxyl groups contained in the silicon sol was confirmed through 1H nuclear magnetic resonance spectroscopy.

[0143]

[0144] Comparative Example 1-2

[0145] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol was used instead of 10 g of ethanol, 120 g of methanol instead of 190 g of methanol, 83.3 g (0.4 mol) of TEOS instead of 10.4 g (0.05 mol) of TEOS, and 81.7 g (0.6 mol) of methyl tirmethoxysilane instead of 224.5 g (0.95 mol) of 3-GPTMS.

[0146] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to methyl groups contained in the silicon sol was 5:5.

[0147]

[0148] Comparative Examples 1-3

[0149] A silicon sol was prepared in the same manner as in Example 1-1, except that 80 g of ethanol was used instead of 10 g of ethanol, 120 g of methanol instead of 190 g of methanol, 83.3 g (0.4 mol) of TEOS instead of 10.4 g (0.05 mol) of TEOS, and 98.6 g (0.6 mol) of Propyl tirmethoxysilane instead of 224.5 g (0.95 mol) of 3-GPTMS.

[0150] It was confirmed that a silicon sol with a sol particle size of about 25 nm was produced in the same manner as in Example 1-1 above, and that the ratio of hydroxyl groups to propyl groups contained in the silicon sol was 5:5.

[0151]

[0152] (1) First functional group Second functional group (1):(2):(3)(2) Reactive functional group (3) Non-reactive functional group Comparative Example 1-1 Hydroxyl group---Comparative Example 1-2 Hydroxyl group-methyl group 5:0:5 Comparative Example 1-3 Hydroxyl group-propyl group 5:0:5

[0153]

[0154] Preparation of a curable composition

[0155] Example 2-1

[0156] Benzyl(4-hydroxyphenyl)methylsulfonium hexafluoroantimonate was prepared as a cationic thermal initiator, and isopropyl alcohol was prepared as a solvent.

[0157] Subsequently, the silicone sol prepared in Example 1-1 and the thermal initiator were added to a solvent and stirred for 1 hour to prepare a curable composition. At this time, based on 100 parts by weight of the solid content of the curable composition, the solid content of the silicone sol was 95.2 parts by weight and the content of the initiator was 4.8 parts by weight.

[0158] Subsequently, a curable composition was applied to the LCD glass and cured in a 150°C drying oven for 5 minutes to obtain a coating layer.

[0159]

[0160] Examples 2-2 to 2-29

[0161] A curable composition and a coating layer were prepared in the same manner as in Example 2-1, except that the type and content of the silicone sol and the content of the initiator were adjusted as shown in Table 3 below.

[0162] Meanwhile, in the case of Example 2-10, compared to Example 2-1, the radical detonator Azobisisobutyronitrile was used instead of the cationic detonator Benzyl(4-hydroxyphenyl)methylsulfonium Hexafluoroantimonate.

[0163]

[0164] Silicone Solvent Type Solid Content (Parts by Weight) Content (Parts by Weight) Example 2-1 Example 1-1 95.24.8 Example 2-2 Example 1-2 95.24.8 Example 2-3 Example 1-3 95.24.8 Example 2-4 Example 1-4 95.24.8 Example 2-5 Example 1-5 95.24.8 Example 2-6 Example 1-6 95.24.8 Example 2-7 Example 1-7 95.24.8 Example 2-8 Example 1-8 95.24.8 Example 2-9 Example 1-9 95.24.8 Example 2-10 Example 1-10 95.24.8 Example 2-11 1-1195.24.8 Example 2-12 Example 1-1295.24.8 Example 2-13 Example 1-1395.24.8 Example 2-14 Example 1-1495.24.8 Example 2-15 Example 1-1595.24.8 Example 2-16 Example 1-1695.24.8 Example 2-17 Example 1-1795.24.8 Example 2-18 Example 1-1895.24.8 Example 2-19 Example 1-1995.24.8 Example 2-20 Example 1-589.011.0 Example 2-21 Example 1-590.99.1 Example 2-22 Example 1-592.67.4 Example 2-23 Example 1-594.35.7 Example 2-24 Example 1-597.12.9 Example 2-25 Example 1-599.01.0 Example 2-26 Example 1-599.70.3 Example 2-27 Example 1-585.714.3 Example 2-28 Example 1-581.118.9 Example 2-29 Example 1-578.921.1

[0165] In Table 3 above, the solid content (parts by weight) of the silicone sol and the content (parts by weight) of the initiator are based on 100 parts by weight of the solid content included in the curable composition.

[0166]

[0167] Comparative Example 2-1

[0168] A curable composition and a coating layer were prepared in the same manner as in Example 2-1, except that the silicone sol prepared in Comparative Example 1-1 was used instead of the silicone sol prepared in Example 1-1.

[0169]

[0170] Comparative Example 2-2

[0171] Azobisisobutyronitrile was prepared as a radical thermal initiator, methyl isobutyl ketone was prepared as a solvent, and MA0735 (Hybrid Plastics), a cage-structured silsesquioxane oligomer, was prepared.

[0172] Subsequently, a silsesquioxane oligomer and a thermal initiator were added to a solvent and stirred for 1 hour to prepare a curable composition. At this time, based on 100 parts by weight of solid content of the curable composition, the content of the silsesquioxane oligomer was 95.2 parts by weight and the content of the initiator was 4.8 parts by weight.

[0173] Subsequently, a curable composition was applied onto a transparent polyimide film (Kolon) with a thickness of 80 μm, and cured in a drying oven at 150°C for 5 minutes to obtain a coating layer.

[0174]

[0175] Comparative Example 2-3

[0176] Benzyl(4-hydroxyphenyl)methylsulfonium hexafluoroantimonate was prepared as a cationic thermal initiator, isopropyl alcohol was prepared as a solvent, and silica nanoparticles of 50 nm size were prepared.

[0177] Subsequently, silica nanoparticles and a thermal initiator were added to a solvent and stirred for 1 hour to prepare a curable composition. At this time, based on 100 parts by weight of the solid content of the curable composition, the content of silica nanoparticles was 95.2 parts by weight and the content of the initiator was 4.8 parts by weight.

[0178] Subsequently, a curable composition was applied onto a transparent polyimide film (Kolon) with a thickness of 80 μm, and cured in a drying oven at 150°C for 5 minutes to obtain a coating layer.

[0179]

[0180] Comparative Example 2-4

[0181] A curable composition and a coating layer were prepared in the same manner as in Example 2-1, except that the cationic thermal initiator Benzyl(4-hydroxyphenyl)methylsulfonium Hexafluoroantimonate was not used.

[0182]

[0183] Comparative Example 2-5

[0184] A curable composition and a coating layer were prepared in the same manner as in Example 2-1, except that the silicone sol prepared in Comparative Example 1-2 was used instead of the silicone sol prepared in Example 1-1.

[0185]

[0186] Comparative Example 2-6

[0187] A curable composition and a coating layer were prepared in the same manner as in Example 2-1, except that the silicone sol prepared in Comparative Example 1-3 was used instead of the silicone sol prepared in Example 1-1.

[0188]

[0189] Preparation of a curable coloring composition

[0190] Example 3-1

[0191] Benzyl(4-hydroxyphenyl)methylsulfonium hexafluoroantimonate was prepared as a cationic thermal initiator, isopropyl alcohol was prepared as a solvent, and copper phthalocyanine (blue) with a particle size of 40 nm was prepared as a coloring agent.

[0192] Subsequently, the silicone sol thermal initiator prepared in Example 1-1 was added to the solvent and stirred for 1 hour, then a coloring agent was added and stirred for 2 more hours to prepare a curable coloring composition. At this time, based on 100 parts by weight of solid content of the curable coloring composition, the solid content of the silicone sol was 91 parts by weight, the content of the initiator was 4.5 parts by weight, and the content of the coloring agent was 4.5 parts by weight.

[0193] Subsequently, a curable coloring composition was applied onto a transparent polyimide film (Kolon) with a thickness of 80 μm, and cured in a drying oven at 150°C for 5 minutes to obtain a colored coating layer.

[0194]

[0195] Examples 3-2 to 3-32

[0196] A curable coloring composition and a coloring coating layer were prepared in the same manner as in Example 3-1, except that the type and content of the silicone sol, the content of the initiator, and the content and size of the coloring agent were controlled as shown in Table 4 below.

[0197] Meanwhile, in the case of Example 3-10, compared to Example 3-1, the radical detonator Azobisisobutyronitrile was used instead of the cationic detonator Benzyl(4-hydroxyphenyl)methylsulfonium Hexafluoroantimonate.

[0198]

[0199] Silicone sol-based coloring agent (1): (2) Type Solid content (parts by weight) Content (parts by weight) Content (parts by weight) Example 3-1 Example 1-19 1.04.54.51:1.6 Example 3-2 Example 1-29 1.04.54.51:1.6 Example 3-3 Example 1-39 1.04.54.51:1.6 Example 3-4 Example 1-49 1.04.54.51:1.6 Example 3-5 Example 1-59 1.04.54.51:1.6 Example 3-6 Example 1-69 1.04.54.51:1.6 Example 3-7 Example 1-79 1.04.54.51:1.6 Example 3-8 Example 1-8 91.04.54.51:1.6 Example 3-9 Example 1-9 91.04.54.51:1.6 Example 3-10 Example 1-10 91.04.54.51:1.6 Example 3-11 Example 1-11 91.04.54.51:1.6 Example 3-12 Example 1-12 91.04.54.51:1.6 Example 3-13 Example 1-13 91.04.54.51:1.6 Example 3-14 Example 1-14 91.04.54.51:1.6 Example 3-15 Example 1-15 91.04.54.51:1.6 Example 3-16 Example 1-16 91.04.54.51:1.6 Example 3-17 Example 1-17 91.04.54.51:1.6 Example 3-18 Example 1-18 91.04.54.51:1.6 Example 3-19 Example 1-19 91.04.54.51:1.6 Example 3-20 Example 1-582.09.09.01:1.6 Example 3-21 Example 1-583.48.38.31:1.6 Example 3-22 Example 1-586.26.96.91:1.6 Example 3-23 Example 1-589.25.45.41:1.6 Example 3-24 Example 1-594.42.82.81:1.6 Example 3-25 Example 1-598.01.01.01:1.6 Example 3-26 Example 1-599.40.30.31:1.6 Example 3-27 Example 1-580.69.79.71:1.6 Example 3-28 Example 1-591.04.54.51:0.1 Example 3-29 Example 1-591.04.54.51:0.5 Example 3-30 Example 1-591.04.54.51:5 Example 3-31 Example 1-591.04.54.51:40 Example 3-32 Example 1-591.04.54.51:0.09.

[0200] In Table 4 above, the solid content (parts by weight) of the silicone sol, the content of the initiator (parts by weight), and the content of the coloring agent (parts by weight) are based on 100 parts by weight of the solid content included in the curable coloring composition. Also, in Table 4 above, (1) is the size of the sol particles included in the silicone sol, (2) is the size of the coloring agent, and “(1):(2)” indicates the ratio of the size of the sol particles included in the silicone sol to the size of the coloring agent.

[0201]

[0202] Comparative Example 3-1

[0203] A curable coloring composition and a coloring coating layer were prepared in the same manner as in Example 3-1, except that the silicone sol prepared in Comparative Example 1-1 was used instead of the silicone sol prepared in Example 1-1.

[0204]

[0205] Comparative Example 3-2

[0206] Azobisisobutyronitrile was prepared as a radical thermal initiator, methyl isobutyl ketone was prepared as a solvent, MA0735 (Hybrid Plastics), a cage-structured silsesquioxane oligomer, was prepared, and copper phthalocyanine (blue) with a particle size of 40 nm was prepared as a coloring agent.

[0207] Subsequently, a silsesquioxane oligomer and a thermal initiator were added to a solvent and stirred for 1 hour, then a coloring agent was added and stirred for 2 more hours to prepare a curable coloring composition. At this time, based on 100 parts by weight of solid content of the curable coloring composition, the content of the silsesquioxane oligomer was 91 parts by weight, the content of the initiator was 4.5 parts by weight, and the content of the coloring agent was 4.5 parts by weight.

[0208] Subsequently, a curable coloring composition was applied onto a transparent polyimide film (Kolon) with a thickness of 80 μm, and cured in a drying oven at 150°C for 5 minutes to obtain a colored coating layer.

[0209]

[0210] Comparative Example 3-3

[0211] Benzyl(4-hydroxyphenyl)methylsulfonium hexafluoroantimonate was prepared as a cationic thermal initiator, isopropyl alcohol was prepared as a solvent, silica nanoparticles of 50 nm size were prepared, and copper phthalocyanine (blue) with a particle size of 40 nm was prepared as a coloring agent.

[0212] Subsequently, silica nanoparticles and a thermal initiator were added to a solvent and stirred for 1 hour, then a coloring agent was added and stirred for 2 more hours to prepare a curable coloring composition. At this time, based on 100 parts by weight of solid content of the curable coloring composition, the content of silica nanoparticles was 91 parts by weight, the content of the initiator was 4.5 parts by weight, and the content of the coloring agent was 4.5 parts by weight.

[0213] Subsequently, a curable coloring composition was applied onto a transparent polyimide film (Kolon) with a thickness of 80 μm, and cured in a drying oven at 150°C for 5 minutes to obtain a colored coating layer.

[0214]

[0215] Comparative Example 3-4

[0216] A curable coloring composition and a coloring coating layer were prepared in the same manner as in Example 3-1, except that the cationic thermal initiator Benzyl(4-hydroxyphenyl)methylsulfonium Hexafluoroantimonate was not used.

[0217]

[0218] Comparative Example 3-5

[0219] A curable coloring composition and a coloring coating layer were prepared in the same manner as in Example 3-1, except that the silicone sol prepared in Comparative Example 1-2 was used instead of the silicone sol prepared in Example 1-1, compared to Example 3-1.

[0220]

[0221] Comparative Example 3-6

[0222] A curable coloring composition and a coloring coating layer were prepared in the same manner as in Example 3-1, except that the silicone sol prepared in Comparative Example 1-3 was used instead of the silicone sol prepared in Example 1-1.

[0223]

[0224] Experimental Example

[0225] Pencil hardness, adhesion, chemical resistance, and optical properties were measured for the curable compositions prepared in the above examples and comparative examples and the coating layer prepared using them, as well as for the curable coloring compositions prepared in the above examples and comparative examples and the coloring coating layer prepared using them, using the following methods. The measured results are listed in Tables 5 to 8 below.

[0226]

[0227] Pencil Hardness Evaluation

[0228] Pencil hardness evaluation was performed on the coating layer and colored coating layer prepared in the above examples and comparative examples using the following method.

[0229] Evaluation was performed under a 750 g load in accordance with JIS 5600-5-4. Mitsubishi pencils were used, and tests were conducted five times per pencil hardness; a pencil was judged defective if two or more scratches occurred. The results were expressed as the measured hardness divided by the number of scratch-free trials.

[0230]

[0231] Adhesion strength evaluation

[0232] In accordance with JIS K5600-5-6, 100 scratches were made in a grid pattern by scratching with a cutter blade at 1 mm intervals, and an adhesive tape was attached to it and then peeled off at a 90° angle to visually check whether the surface of the coating layer adhered to the adhesive tape and peeled off.

[0233] Tables 5 and 7 below indicate the number of items that did not fall out of 100. It is indicated as the number of items that did not fall out / 100, and for example, if 100 items did not fall out, it is indicated as 100 / 100.

[0234]

[0235] Chemical resistance evaluation

[0236] For the coating layer and colored coating layer prepared in the above examples and comparative examples, 50, 70, and 100 reciprocating passes were performed with a 1 kg load using a dust-free cloth soaked in ethanol.

[0237] Subsequently, the specimens subjected to evaluation were examined under a microscope; if the coating layer did not peel off, it was judged as Pass, and if the coating layer peeled off, it was judged as Failure.

[0238]

[0239] Dispersion stability evaluation

[0240] The curable coloring compositions prepared in the above examples and comparative examples were stored in an oven at 25°C for 30, 60, and 120 days, and then the presence or absence of precipitation of the coloring agent was checked.

[0241] - Rated as X if sediment is detected

[0242] - Rated as O if there is no precipitate

[0243]

[0244] Measurement of optical properties

[0245] For the coating layers and colored coating layers prepared in the above examples and comparative examples, optical properties were measured in transmission mode using a colorimeter (Minolta CM-3700A). Measurements were taken 5 times per sample, and the average values ​​are listed in Tables 6 and 7 below.

[0246]

[0247] Coating Thickness Pencil Hardness Evaluation Adhesion Evaluation Chemical Resistance Evaluation (100 Cycles) LCD Glass-9H (5 / 5) -- Example 2-11㎛ 7H ​​(4 / 5) pass (100 / 100) Pass Example 2-21㎛ 7H ​​(5 / 5) pass (100 / 100) Pass Example 2-31㎛ 8H (4 / 5) pass (100 / 100) Pass Example 2-41㎛ 8H (5 / 5) pass (100 / 100) Pass Example 2-51㎛ 9H (5 / 5) pass (100 / 100) Pass Example 2-61㎛ 9H (5 / 5) pass (100 / 100) Pass Example 2-71㎛ 9H (5 / 5) pass (100 / 100) Pass Example 2-81㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-91㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-101㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-111㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-121㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-131㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-141㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-151㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-161㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-171㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-181㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-191㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-201㎛ 7H(4 / 5)pass(100 / 100)Pass Example 2-211㎛ 8H(4 / 5)pass(100 / 100)Pass Example 2-221㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-231㎛ 9H(5 / 5)pass(100 / 100)Pass Example 2-241㎛ 9H (5 / 5)pass (100 / 100)Pass Example 2-251㎛ 8H (5 / 5)pass (100 / 100)Pass Example 2-261㎛ 7H ​​(5 / 5)pass (100 / 100)Pass Example 2-271㎛ 7H ​​(4 / 5)pass (100 / 100)Pass Example 2-281㎛ 6H (5 / 5)pass (100 / 100)Pass Example2-29 1㎛ 6H(4 / 5)pass(100 / 100)Pass Comparative Example 2-11㎛ Film Formation X--Comparative Example 2-21㎛ Adhesion Failure--Comparative Example 2-31㎛ Film Formation X--Comparative Example 2-41㎛ Curing X--Comparative Example 2-51㎛ 9B(0 / 5)pass(100 / 100)Failure Comparative Example 2-61㎛ 9B(0 / 5)pass(100 / 100)Failure

[0248]

[0249] Optical Properties 550 nm Transmittance (%) YI(E313-73) a* b* LCD Glass 9 2.36 0.09 0.00 0.14 Example 2-1 9 2.45 0.10 -0.03 0.14 Example 2-2 9 2.43 0.11 -0.02 0.16 Example 2-3 9 2.39 0.12 -0.01 0.15 Example 2-4 9 2.41 0.10 -0.02 0.15 Example 2-5 9 2.40 0.10 -0.04 0.14 Example 2-6 9 2.42 0.11 -0.02 0.16 Example 2-7 9 2.46 0.12 -0.01 0.16 Example 2-892.450.10-0.020.15 Example 2-992.380.130.000.17 Example 2-1092.440.12-0.010.16 Example 2-1192.420.11-0.010.15 Example 2-1292.420.13-0.020.17 Example 2-1392.440.10-0.030.15 Example 2-1492.410.12-0.010.16 Example 2-1592.450.110.000.14 Example 2-1692.430.10-0.010.13 Example 2-1792.430.12-0.010.15 Example 2-1892.420.11-0.020.15 Example 2-1992.390.13-0.020.17 Example 2-2092.410.12-0.010.16 Example 2-2192.440.11-0.020.15 Example 2-2292.380.14-0.010.17 Example 2-2392.400.11-0.020.16 Example 2-2492.420.11-0.010.15 Example 2-2592.390.13-0.010.16 Example 2-2692.430.12-0.030.15 Example 2-2792.410.13-0.020.17 Example 2-2892.390.14-0.010.19 Example 2-2992.360.16-0.000.21 Comparative Example 2-1 Film formation X--- Comparative Example 2-2 Adhesion failure--- Comparative Example 2-3 Film formation X--- Comparative Example 2-4 Curing X--- Comparative Example 2-592.410.13-0.010.16 Comparative Example 2-692.430.11-0.010.15

[0250] Referring to Tables 5 and 6 above, it was confirmed that the curable compositions prepared in Examples 2-1 to 2-29 had excellent hardness, adhesion, chemical resistance, and optical properties.

[0251] On the other hand, in the case of Comparative Examples 2-1 to 2-6, it was confirmed that the physical properties were inferior compared to Examples 2-1 to 2-26. Specifically, it was confirmed that the curable compositions of Comparative Example 2-1 and Comparative Example 2-3 failed to form a coating layer. In the case of Comparative Example 2-2, adhesion was not achieved, and in Comparative Example 2-4, it was confirmed that it was not cured. In the case of Comparative Examples 2-5 and 2-6, it was confirmed that the chemical resistance was very inferior.

[0252]

[0253] Dispersion Stability Evaluation (Day) Coating Thickness Pencil Hardness Evaluation 3060 120 CPI Film (80 µm) ---- 4H (4 / 5) Example 3 - 1000 1 µm 3H (4 / 5) Example 3 - 2000 1 µm 3H (5 / 5) Example 3 - 3000 1 µm 4H (4 / 5) Example 3 - 4000 1 µm 4H (5 / 5) Example 3 - 5000 1 µm 5H (5 / 5) Example 3 - 6000 1 µm 5H (5 / 5) Example 3 - 7000 1 µm 5H (5 / 5) Example 3 - 8000 1 µm 5H (5 / 5) Example 3 - 9000 1 µm 5H (5 / 5) Example 3 - 1000 1 µm 5H (5 / 5) Example 3 - 11000 1 µm 5H (5 / 5) Example Example 3-12000 1㎛ 5H (5 / 5) Example 3-13000 1㎛ 5H (5 / 5) Example 3-14000 1㎛ 5H (5 / 5) Example 3-15000 1㎛ 5H (5 / 5) Example 3-16000 1㎛ 5H (5 / 5) Example 3-17000 1㎛ 5H (5 / 5) Example 3-18000 1㎛ 5H (5 / 5) Example 3-19000 1㎛ 5H (5 / 5) Example 3-20000 1㎛ 3H (4 / 5) Example 3-21000 1㎛ 4H (5 / 5) Example 3-22000 1㎛ 5H (5 / 5) Example 3-23000 1㎛ 5H (5 / 5) Example 3-24OOO1㎛5H(5 / 5) Example 3-25OOO1㎛4H(5 / 5) Example 3-26OOO1㎛3H(5 / 5) Example 3-27OOO1㎛3H(4 / 5) Example 3-28OOO1㎛3H(4 / 5) Example 3-29OOO1㎛5H(5 / 5) Example 3-30OOO1㎛5H(5 / 5) Example 3-31OOOX1㎛3H(5 / 5) Example 3-32OX-1㎛5H(5 / 5) Comparative Example 3-1X--1㎛ Film Formation X Comparative Example 3-2X--1㎛ Adhesion Failure Comparative Example 3-3X--1㎛ Film Formation X Comparative Example 3-4O1㎛ Curing X Comparative Example 3-5 OXX 1㎛ 9B (0 / 5) Comparative Example 3-6 OXX 1㎛ 9B (0 / 5)

[0254]

[0255] Adhesion Evaluation Chemical Resistance Evaluation (Recovery) 50 70 100 CPI Film (80um) ---- Example 3 - 1 pass (100 / 100) Pass Pass Pass Example 3 - 2 pass (100 / 100) Pass Pass Pass Example 3 - 3 pass (100 / 100) Pass Pass Pass Example 3 - 4 pass (100 / 100) Pass Pass Pass Example 3 - 5 pass (100 / 100) Pass Pass Pass Example 3 - 6 pass (100 / 100) Pass Pass Pass Example 3 - 7 pass (100 / 100) Pass Pass Pass Example 3 - 8 pass (100 / 100) Pass Pass Pass Example 3 - 9 pass (100 / 100) Pass Pass Pass Example 3 - 10 pass (100 / 100) Pass Pass Pass Example 3-11 pass(100 / 100) Pass Pass Pass Example 3-12 pass(100 / 100) Pass Pass Pass Example 3-13 pass(100 / 100) Pass Pass Pass Example 3-14 pass(100 / 100) Pass Pass Pass Example 3-15 pass(100 / 100) Pass Pass Pass Example 3-16 pass(100 / 100) Pass Pass Pass Example 3-17 pass(100 / 100) Pass Pass Pass Example 3-18 pass(100 / 100) Pass Pass Pass Example 3-19 pass(100 / 100) Pass Pass Pass Example 3-20 pass(100 / 100) Pass Pass Pass Example 3-21 pass(100 / 100) Pass Pass Pass Example 3-22 pass(100 / 100)PassPassPass Example 3-23 pass(100 / 100)PassPassPass Example 3-24 pass(100 / 100)PassPassPass Example 3-25 pass(100 / 100)passPassPass Example 3-26 pass(100 / 100)passPassPass Example 3-27 pass(100 / 100)PassPassPass Example 3-28 pass(100 / 100)PassPassPass Example 3-29 pass(100 / 100)PassPassPass ExampleExample 3-30 pass(100 / 100) passPassPass Example 3-31 pass(100 / 100) PassFailure- Example 3-32 pass(100 / 100) PasspassFailure Comparative Example 3-1----Comparative Example 3-2----Comparative Example 3-3----Comparative Example 3-4----Comparative Example 3-5 pass(100 / 100)Failure--Comparative Example 3-6 pass(100 / 100)Failure--

[0256]

[0257] Optical Properties 550 nm Transmittance (%) YI(E313-73) a*b* CPI Film (80 µm) 88.86 2.78 -0.63 1.97 Example 3-19 0.25 0.20 -1.06 0.56 Example 3-29 0.22 0.18 -1.06 0.59 Example 3-39 0.18 0.22 -1.04 0.66 Example 3-49 0.20 0.19 -1.03 0.62 Example 3-59 0.27 0.14 -1.05 0.47 Example 3-69 0.19 0.21 -1.05 0.63 Example 3-79 0.21 0.18 -1.03 0.54 Example 3-890.180.24-1.060.63 Example 3-990.240.16-1.030.56 Example 3-1090.270.15-1.030.48 Example 3-1190.190.24-1.050.66 Example 3-1290.210.18-1.040.55 Example 3-1390.250.17-1.030.54 Example 3-1490.230.17-1.030.53 Example 3-1590.220.19-1.040.55 Example 3-1690.200.20-1.050.59 Example 3-1790.260.15-1.030.49 Example 3-1890.250.15-1.040.51 Example 3-1990.220.21-1.030.61 Example 3-2090.190.23-1.060.64 Example 3-2190.210.19-1.040.53 Example 3-2290.230.17-1.030.51 Example 3-2390.220.18-1.040.52 Example 3-2490.240.17-1.030.52 Example 3-2590.230.17-1.050.51 Example 3-26 90.23 0.18 -1.03 0.52 Example 3-27 90.20 0.24 -1.03 0.61 Example 3-28 90.24 0.19 -1.07 0.51 Example 3-29 90.22 0.16 -1.04 0.58 Example 3-30 90.19 0.20 -1.06 0.63 Example 3-31 90.18 0.26 -1.01 0.68 Example 3-32 90.21 0.21 -1.02 0.55 Comparative Example 3-1 Film formation X----Comparative Example 3-2 Adhesion failure----Comparative Example 3-3 Film formation X----Comparative Example 3-4 Curing X----Comparative Example 3-590.200.21-1.050.64 Comparative Example 3-690.220.20-1.040.61.

[0258] Referring to Tables 7 to 9 above, it was confirmed that the curable compositions prepared in Examples 3-1 to 3-32 exhibited excellent dispersion stability, hardness, adhesion, chemical resistance, and optical properties.

[0259] On the other hand, it was confirmed that the physical properties of Comparative Examples 3-1 to 3-6 were inferior compared to Examples 3-1 to 3-26. Specifically, it was confirmed that the curable compositions of Comparative Example 3-1 and Comparative Example 3-3 had inferior dispersion stability and failed to form a coating layer. In the case of Comparative Example 3-2, no adhesion was achieved, and in Comparative Example 3-4, it was confirmed that no curing occurred. In the case of Comparative Examples 3-5 and 3-6, it was confirmed that the chemical resistance was very inferior.

[0260]

[0261] Therefore, it can be seen that the curable composition according to one embodiment of the present invention has excellent dispersion stability and can effectively realize a coating layer with improved mechanical properties such as hardness and adhesion, chemical resistance, and optical properties.

Claims

1. A silicone sol containing a first functional group comprising one or more functional groups including a hydroxyl group and a second functional group comprising one or more reactive functional groups other than a hydroxyl group; and A curable composition comprising an initiator.

2. In Paragraph 1, The above silicon sol is, A curable composition having a ratio of the first functional group to the second functional group of 1:9 to 9:

1.

3. In Paragraph 1, The above silicon sol is, A curable composition in which the ratio of the first functional group to the second functional group exceeds 1.

4. In Paragraph 1, A curable composition wherein the second functional group comprises at least one reactive functional group selected from an amino group, a (meth)acrylate group, a vinyl group, an epoxy group, and a thiol group.

5. In Paragraph 4, A curable composition wherein the second functional group further comprises at least one non-reactive functional group selected from a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms and an aromatic group having 6 to 30 carbon atoms.

6. In Paragraph 1, It further contains coloring agents, A curable composition in which the ratio of the size of the sol particles included in the silicone sol to the size of the coloring agent is 1:0.01 to 1:

5.

7. In Paragraph 1, A curable composition having a silicone sol content of 80 parts by weight or more based on 100 parts by weight of the solid content of the above curable composition.

8. In Paragraph 1, A curable composition having a content of 0.1 parts by weight or more and 20 parts by weight or less of the initiator, based on 100 parts by weight of the solid content of the above curable composition.

9. In Paragraph 1, It further contains coloring agents, A curable composition having a content of 0.1 parts by weight or more and 10 parts by weight or less, based on 100 parts by weight of the solid content of the above curable composition.

10. A coating layer comprising a cured product of the curable composition according to claim 1.