JPH06136062A - Fluorine-containing curable composition and fluorine-containing cured coating film - Google Patents

Abstract

PURPOSE:To provide a composition containing a specific fluorine-containing (meth)acrylic acid ester and a curable component, having excellent weather resistance and heatresistance and giving a light-transmitting fluorine-containing cured coating film having high surface hardness and low refractive index. CONSTITUTION:The composition contains (A) 50-95wt.% of a fluorine-containing (meth)acrylic acid ester of the formula CH2=CX-COOY (X is H or methyl; Y is 2-12C fluoroalkyl having >=3 F atoms or 4-12C fluorocycloalkyl having >=4 F atoms) [preferably 2,2,2-trifluoroethyl (meth)acrylate, etc.] and (B) 5-50wt.% of a curable component [preferably hexanediol di(meth)acrylate, etc.]. The compound A can be produced e.g. by esterifying (meth)acrylic acid with a fluorine-containing alcohol.

Description

Detailed Description of the Invention

[0001]

The present invention has a high surface hardness,
The present invention relates to a fluorine-containing cured coating that can be used on the surface of various substrates and the like, and a fluorine-containing curable composition that can be used as a raw material for the cured coating.

[0002]

2. Description of the Related Art Fluorocarbons have a very strong C—F bond and are chemically stable due to the strong electron-withdrawing property of the fluorine atom, and they have an interaction force (van der
Since it does not have a Waals force), it exhibits properties different from hydrocarbon-based substances, such as low viscosity and high volatility. These properties due to the fluorine atom are similarly expressed not only in the low molecular weight substance but also in the high molecular weight substance, that is, the resin having a large number of fluorine atoms (fluorine resin). In particular, a fluororesin is used for a low refractive index film or the like by utilizing its low refractive index, chemical stability, heat resistance and the like.

However, polymers having a fluorine atom introduced into the polymer main chain such as trifluoroethylene, vinylidene fluoride, and perfluoroethylene polymers are excellent in heat resistance and chemical stability, When it is used for treating a material such as a thermoplastic resin that needs to be heat-processed, it has a problem of poor workability and poor solubility in an organic solvent. Furthermore, metal, plastic, glass,
When the surface of a material such as wood is coated with the fluororesin for surface treatment, it is necessary to heat and melt the fluororesin once and then mechanically compress it. Cannot be coated and is not suitable for a mechanically brittle substrate such as glass, which poses a problem that the materials that can be coated are limited. Further, since these polymers are opaque or have a refractive index higher than 1.44, they are unsuitable as low refractive index coating resins which require transparency.

Therefore, for the purpose of improving the thermal processability and the solubility in organic solvents, it has been proposed to copolymerize a perfluoroethylene monomer with another monomer. Therefore, the heat resistance is poor, the solubility in an organic solvent is insufficient, and a sufficient refractive index is not obtained.

Further, a polymerizable monomer having a perfluoroalkyl group in its side chain, for example, a polymer containing an acrylic acid fluorine-containing alkyl ester or a methacrylic acid fluorine-containing alkyl ester or a polymer containing a fluorine-containing alkylstyrene has been proposed. There is.

However, although the polymer containing a fluorine-containing alkylstyrene or the like has improved solubility in an organic solvent, it has long-term stability (weather resistance) because the aromatic group absorbs ultraviolet rays and a deterioration reaction proceeds. In addition, since the aromatic group exhibits a high refractive index, it is unsuitable as a resin having a low refractive index. On the other hand, although the fluorine-containing alkyl ester has a low refractive index, it has a drawback that it has poor wear resistance because of its low surface hardness.

[0007]

The object of the present invention is to provide a low-refractive-index fluorine-containing cured coating having excellent weather resistance and heat resistance, high surface hardness, and light transmission, and a raw material for the cured coating. It is to provide a possible fluorine-containing curable composition.

[0008]

According to the present invention, the following general formula 3 (wherein X represents a hydrogen atom or a methyl group, and Y
Is a C2-C12 fluoroalkyl group having 3 or more fluorine atoms or a C4-C4 carbon atom having 4 or more fluorine atoms.
12 shows a fluorocycloalkyl group. 50% to 95% by weight of a fluorine-containing (meth) acrylic acid ester represented by the formula (hereinafter referred to as "ester 1") or a fluorine-containing polymer containing the ester 1 as a constituent, and a curable component 5
There is provided 50% by weight of a fluorine-containing curable composition.

[0009]

[Chemical 3]

According to the present invention, the pencil hardness obtained by polymerizing and curing the fluorine-containing curable composition has a surface hardness of H or more and a refractive index of 1.44 or less. A cured coating is provided.

The present invention will be described in more detail below.

The fluorinated curable composition of the present invention is a composition containing a fluorinated (meth) acrylic acid ester having a specific structure and a specific amount, and a curable component (hereinafter referred to as composition A).
Alternatively, a composition (hereinafter referred to as composition B) containing a specific amount of a fluoropolymer containing a fluorine-containing (meth) acrylic ester of a specific structure as a constituent and a curable component,
When polymerized, it does not have a methylene group in the part that becomes the main chain structure, a substituent is bonded to the carbon of the main chain, the glass transition temperature is high, and it is difficult to attack the side chain bond, It is possible to obtain a polymer having excellent properties and weather resistance.

The fluorine-containing (meth) acrylic acid ester used in the composition A and the composition B is the ester 1 represented by the general formula 3. When the carbon number of Y in the ester 1 is 13 or more, the production is difficult. Specific examples of the ester 1 include (meth) acrylic acid-2,2,2-trifluoroethyl, (meth) acrylic acid-2,2,3,3,3-pentafluoropropyl, (meth) ) Acrylic acid-2,2,3,3,4,4,4
-Heptafluorobutyl, (meth) acrylic acid-2,
2,3,3,4,4,5,5,5-nonafluoropentyl, (meth) acrylic acid-2,2,3,3,4,4,4
5,5,6,6,6-undecafluorohexyl, (meth) acrylic acid-2,2,3,3,4,4,5,5
6,6,7,7,7-Tridecafluoroheptyl, (meth) acrylic acid-2,2,3,3,4,4,5,5,5
6,6,7,7,8,8,8-pentadecafluorooctyl, (meth) acrylic acid-3,3,4,4,5,5,5
6,6,7,7,8,8,8-tridecafluorooctyl, (meth) acrylic acid-2,2,3,3,4,4,4
5,5,6,6,7,7,8,8,9,9,10,1
0,10-nonadecafluorodecyl, (meth) acrylic acid-3,3,4,4,5,5,6,6,7,7,8,
8,9,9,10,10,10-heptadecafluorodecyl, (meth) acrylic acid-2-trifluoromethyl-
3,3,3-trifluoropropyl, (meth) acrylic acid-3-trifluoromethyl-4,4,4-trifluorobutyl, (meth) acrylic acid-1-methyl-2,2,2
3,3,3-Pentafluoropropyl, (meth) acrylic acid-1-methyl-2,2,3,4,4,4-heptafluorobutyl, (meth) acrylic acid-2,2,3,3
3,4,4-hexafluorocyclobutyl, (meth) acrylic acid-2,2,3,3,4,4,5,5-octafluorocyclopentyl, (meth) acrylic acid-2,2
3,3,4,4,5,5,6,6-decafluorocyclohexyl, (meth) acrylic acid-2,2,3,3,4
4,5,5,6,6,7,7-dodecafluorocycloheptyl, (meth) acrylic acid-2,2,3,3,4
4,5,5,6,6,7,7,8,8-tetradecafluorocyclooctyl, (meth) acrylic acid-2-trifluoromethylcyclobutyl, (meth) acrylic acid-3-
Trifluoromethylcyclobutyl, (meth) acrylic acid-2-trifluoromethylcyclopentyl, (meth) acrylic acid-3-trifluoromethylcyclopentyl,
(Meth) acrylic acid-2-trifluoromethylcyclohexyl, (meth) acrylic acid-3-trifluoromethylcyclohexyl, (meth) acrylic acid-4-trifluoromethylcyclohexyl, (meth) acrylic acid-2-trifluoromethyl Cycloheptyl, (meth) acrylic acid-3-trifluoromethylcycloheptyl, (meth) acrylic acid-4-trifluoromethylcycloheptyl and the like can be preferably mentioned, and when used, they can be used alone or as a mixture. To prepare such an ester 1, for example, (meth) acrylic acid and
The corresponding fluorine-containing alcohol can be easily obtained by a usual esterification reaction or the like.

In the fluorine-containing curable composition of the present invention,
In the composition A, the ester 1 is blended in a proportion of 50 to 95% by weight, preferably 70 to 90% by weight, based on the total amount of the composition. At this time, when the compounding amount of the ester 1 is less than 50% by weight, a desired low refractive index cured coating cannot be obtained when polymerized and cured, and when it exceeds 95% by weight, the mechanical strength of the cured coating obtained is high. descend. On the other hand, in the composition B, the fluoropolymer containing the ester 1 as a constituent component is 50 to 95% by weight, preferably 70 to 9% by weight in the composition.
It is blended at a ratio of 0% by weight. 50-95% by weight
Outside of the range, the same problems as those of the composition A occur.

The above-mentioned fluoropolymer may be either a polymer of ester 1 or a polymer of ester 1 and other copolymerizable component, preferably having an average molecular weight of 1
It is preferably 000 to 300,000, and is a polymer having a constituent unit of ester 1 of 50% by weight or more, particularly 70% by weight or more. At this time, as the other copolymerization component,
Olefin, (meth) acrylic acid and their alkyl esters; unsaturated polybasic acids such as fumaric acid, maleic acid, citraconic acid, mesaconic acid, itaconic acid, tetrahydrophthalic acid and their alkyl esters, vinyl esters of fatty acids, styrene Preferred examples thereof include vinyl halides, vinyl halides, vinylidene halides, vinyl alkyl ethers, vinyl alkyl ketones, and butadienes. Specific examples include ethylene, propylene, methyl acrylate, butyl acrylate, methyl methacrylate, and methacrylic acid. Butyl acid, acrylonitrile, methacrylonitrile, vinyl acetate, vinyl propionate, vinyl stearate, vinyl pivalate, styrene, α-methylstyrene, vinyl chloride, vinylidene chloride, aryl acetate, vinyl butyl ether Vinyl methyl ketone, vinyl ethyl ketone, vinyl carbazole, 1,3-butadiene,
Isobrene and the like can be preferably mentioned, and particularly vinyl acetate, vinyl propionate, vinyl pivalate, styrene, vinyl butyl ether, vinyl methyl ketone, butadiene and the like are preferable from the viewpoint of copolymerizability. Further, it is preferable to use a copolymerizable monomer other than the ester 1 in which fluorine or a fluoroalkyl group is introduced into these monomers in order to realize a low refractive index.

In order to prepare the above-mentioned fluoropolymer, the desired ester 1 and, if necessary, other copolymerization components can be easily synthesized by a generally used radical polymerization method or the like. Specifically, radical polymerization initiators, for example, azo radical polymerization initiators such as azobisisobutyronitrile, azobiscyclohexanecarbonitrile, and azobisvaleronitrile; benzoyl peroxide, tert-butyl hiddle peroxide, cumene Organic peroxide-based radical polymerization initiators such as peroxides and diacyl peroxides;
Solution polymerization, bulk polymerization, emulsion polymerization using various radical polymerization initiator systems such as inorganic radical polymerization initiators such as ammonium persulfate and potassium persulfate or redox initiators such as hydrogen peroxide-sodium hydroxide system. Radical polymerization methods such as suspension polymerization, radiation polymerization and the like, preferably 10 to 1
It can be synthesized by carrying out a reaction at 00 ° C. for 1 to 100 hours.

As the curable component to be blended in the composition A and the composition B of the present invention, for example, a polymerizable unsaturated group of 2
Or more polyfunctional monomers, specifically, hexanediol di (meth) acrylate, nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, tricyclode di (meth) acrylate Preferable examples include candimethanol, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (acryloyloxyethyl) isocyanurate, divinylben and diethylene glycol di (meth) acrylate. The compounding ratio of the curable component is in the range of 5 to 50% by weight, preferably 5 to 30% by weight in each of the compositions A and B. When the compounding ratio of the curable component exceeds 50% by weight, the refractive index increases when polymerized and cured, and a desired cured film cannot be obtained.

In the composition A and the composition B of the present invention, in addition to the above-mentioned essential components, other copolymerizable raw material components can be blended if necessary. Specifically, for example, the monomers or (meth) acrylic acid listed as other copolymerizable components usable in the fluoropolymer,
Homopolymers or copolymers of unsaturated polybasic acids such as fumaric acid, maleic acid, citraconic acid, mesaconic acid, itaconic acid, tetrahydrophthalic acid and their alkyl esters can be mentioned. The content of the other copolymerizable raw material component is preferably 30% by weight or less. By blending the homopolymer or the copolymer as another copolymerizable raw material component, the viscosity of the composition A and the composition B can be increased and the operability during use can be enhanced.

The fluorine-containing cured film of the present invention is obtained by polymerizing and curing the above composition A or composition B,
It has a surface hardness of pencil hardness H or higher and a refractive index of 1.44 or lower. The average molecular weight of the fluorine-containing cured film is preferably 1000 to 300000, and the film thickness is 1 to 2
It is desirable that the thickness is 000 μm.

To prepare the fluorine-containing cured coating film of the present invention, for example, composition A or composition B or, if necessary, a solvent, a curing initiator, etc. are added, and then coated on a substrate, dried and heated. Alternatively, it can be obtained by curing by irradiation with active energy rays such as ultraviolet rays, electron beams, and radiation.

Examples of the solvent include 1,1,2-trichloro-1,2,2-trifluoroethane, trifluoromethylbenzene and 1,4-bis (trifluoromethyl) benzene. Further, as the curing initiator, the radical polymerization initiators specifically listed above and the like can be used. Further, the base material is not particularly limited, but for example, inorganic materials such as glass, stone, concrete, tiles; vinyl chloride resin, polyethylene terephthalate, polyolefin resin, (meth)
Acrylic resin, poly (meth) acrylic acid ester resin,
Synthetic resins such as phenol resin, xylene resin, urea resin, melamine resin, epoxy resin, silicone resin, diallyl phthalate resin, furan resin, amino resin, alkyd resin, urethane resin, vinyl ester resin, polyimide resin; iron, aluminum, copper Examples of the metal include wood, paper, and the like.

Furthermore, the drying and heating conditions are from room temperature to 2
It is preferably carried out in the range of 00 ° C.

[0023]

Since the fluorine-containing curable composition of the present invention contains a specific fluorine-containing unsaturated dibasic acid diester monomer or polymer as a main component, it is cured to have weather resistance and heat resistance. It is particularly effective as an antireflection coating material having excellent water and oil repellency, high surface hardness, excellent abrasion resistance, low refractive index and light transmittance.

Further, the fluorine-containing cured film of the present invention can be widely used for glass, metal, synthetic resin and the like used in buildings, automobiles, electric appliances and the like. Further, since it has a low surface energy peculiar to a fluoropolymer and is excellent in stain resistance, it can also be applied to biocompatible materials with little protein adsorption, medical instruments, clinical laboratory instruments and the like.

[0025]

The present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

[0026]

Example 1 Methacrylic acid-3,3,3 as ester 1
4,4,5,5,6,6,7,7,8,8,9,9,1
8.5 g of 0,10,10-heptadecafluorodecyl and 1.4 g of trimethylolpropane trimethacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) as a curable component were mixed,
A fluorinated curable composition was prepared.

Then, 0.1 g of benzoyl peroxide as a curing initiator was mixed with the obtained composition, and the thickness was applied onto a polyethylene terephthalate (PET) film by using a thin film coating apparatus (manufactured by Sugiyama Gen-Igiki Co., Ltd.). It was applied so as to have a thickness of 50 μm. Then, heat at 100 ℃ for 2 hours,
Curing was performed to prepare a fluorine-containing cured film. The pencil hardness of the obtained fluorine-containing cured film was measured according to JIS K5400. Further, the fluorine-containing coating was peeled off from the PET sheet, and the refractive index was measured using an Abbe refractometer (manufactured by Atago Co., Ltd.). Further, the contact angle to pure water was measured using a contact angle meter (manufactured by Kyowa Kagaku Co., Ltd.). The results are shown in Table 1.

[0028]

Examples 2 to 4 Ester 1 shown in Table 1, a curable component,
A fluorine-containing curable composition and a fluorine-containing cured film were prepared in the same manner as in Example 1 except that a curing initiator was used. The refractive index, pencil hardness and contact angle of the obtained cured coating were measured in the same manner as in Example 1. The results are shown in Table 1.

[0029]

[Examples 5 and 6] A solution of the fluorine-containing curable composition was prepared in the same manner as in Example 1 except that the ester 1, the curable component, and the curing initiator shown in Table 1 were used. Coated. After drying, UV irradiator (O
33 by RC, trade name "UV-330API")
Ultraviolet rays of 0 nm were irradiated at 1000 mJ / cm ² . After photocuring, each measurement was performed in the same manner as in Example 1. The results are shown in Table 1.

[0030]

Examples 7 and 8 A solution of a fluorine-containing curable composition was prepared in the same manner as in Example 1 except that the ester 1 and the curable components shown in Table 1 were used, and the solution was coated on a PET film. After drying, the accelerator voltage was 174 kV and the beam current was 2 mA with an electron beam irradiator (manufactured by Iwasaki Electric Co., Ltd.).
It was irradiated with an electron beam. The absorbed dose was 4.2 Mrad. After curing, each measurement was performed in the same manner as in Example 1. The results are shown in Table 1.

[0031]

Examples 9 to 11 From the fluorine-containing curable composition in the same manner as in Example 1, except that the ester 1, the curable component, the curing initiator, and the other copolymerizable raw material components shown in Table 1 were used. Each solution was prepared, coated on a PET film, heat-cured, and each measurement was performed. The results are shown in Table 1.

[0032]

[Comparative Examples 1 and 2] Trimethylolpropane trimethacrylate (Comparative Example 1) or acrylic acid-3, 3, 4,
4,5,5,6,6,7,7,8,8,9,9,10,
Each of 9.9 g of 10,10-heptadecafluorodecyl (Comparative Example 2) was taken, 0.1 g of benzoyl peroxide was mixed as a curing initiator, and a thin film coating apparatus (manufactured by Sugiyama Gen Medical Co., Ltd.) was used. Each solution was applied on a PET film so that the thickness of each solution was 50 μm. After drying, each measurement was performed on the obtained coating in the same manner as in Example 1. The results are shown in Table 1.
Shown in.

The abbreviations in Table 1 indicate the following compounds, respectively.

F ₁₇ M; methacrylic acid-3,3,4,4,
5,5,6,6,7,7,8,8,9,9,10,1
0,10-Heptadecafluorodecyl F ₁₇ A; acrylic acid-3,3,4,4,5,5,6
6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl St; styrene TMPTM; trimethylolpropane trimethacrylate TMPTA; trimethylolpropane triacrylate BPO; benzoyl peroxide DAR. 1116; Product name "DAROCUR 1116"
(Merck)

[0035]

[Table 1]

[0036]

Example 2-1 Methacrylic acid-3,3,4,4,5,5
5,6,6,7,7,8,8,9,9,10,10,1
8.5 g of 0-heptadecafluorodecyl was charged into a glass ampoule, 0.05 part by weight of isopropyl peroxide as a radical polymerization initiator was charged, and nitrogen substitution was sufficiently performed, and after depressurizing deaeration was repeated, The ampoule was sealed. Next, the ampoule was placed in a shaking constant temperature bath at 40 ° C. and radical polymerization was carried out for 30 hours. After completion of the polymerization, put the trade name "CG Triflon" (manufactured by Central Glass Co., Ltd.) in an ampoule, dissolve the generated polymer into a solution, and then pour into a large amount of methanol to precipitate the polymer, The polymer was isolated, and reprecipitation was repeated with a CG triflon-methanol system, followed by drying under reduced pressure to obtain a fluoropolymer, polymethacrylic acid-3,3,4,4,5,5,5.
6,6,7,7,8,8,9,9,10,10,10-
Heptadecafluorodecyl (molecular weight 100,000) was obtained. Next, 8.5 g of the obtained fluoropolymer and 1.4 g of trimethylolpropane trimethacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) were mixed as a curable component to prepare a fluorocurable composition.

Next, 0.1 g of benzoyl peroxide as a curing initiator was added to the obtained composition and dissolved in 100 ml of 1,3-bis (trifluoromethyl) benzene, and then a thin film coating apparatus (Sugiyama Motoi) (Manufactured by Kikai Co., Ltd.) was applied to a PET film so as to have a thickness of 500 μm. After drying, it was heated at 100 ° C. for 2 hours and cured to prepare a fluorine-containing cured coating. Various measurements were performed on the obtained cured coating in the same manner as in Example 1. The results are shown in Table 2.

[0038]

[Examples 2-2 to 2-4] The fluoropolymers shown in Table 2,
Example 2-1 except that a curable component and a curing initiator were used.
A solution containing the fluorine-containing curable composition was prepared in the same manner as above, and the solution was coated on a PET film and heat-cured to form a fluorine-containing cured film. Each measurement was performed on the obtained cured film in the same manner as in Example 1. The results are shown in Table 2.

[0039]

Examples 2-5 and 2-6 Example 2 was repeated except that the fluoropolymer, the curable component and the curing initiator shown in Table 2 were used.
A solution containing the fluorine-containing curable composition was prepared in the same manner as in -1, and was coated on a PET film. After drying
UV irradiator (manufactured by ORC, trade name "UV-330AP
I ”) to emit UV light of 330 nm at 1000 mJ / cm
Irradiated ² times. After photocuring, the same measurements as in Example 1 were performed on the obtained fluorine-containing cured coating. The results are shown in Table 2.

[0040]

Examples 2-7 and 2-8 A solution containing a fluorine-containing curable composition was prepared in the same manner as in Example 2-1 except that the fluoropolymers and curable components shown in Table 2 were used. , PET
Coated on film. After drying, an electron beam was irradiated with an electron beam irradiator (manufactured by Iwasaki Electric Co., Ltd.) at an accelerator voltage of 174 kV and a beam current of 2 mA. Absorbed dose is 4.2 Mr
It was ad. After the curing, each measurement was performed on the obtained fluorine-containing cured film in the same manner as in Example 1. The results are shown in Table 2.

[0041]

Examples 2-9 to 2-11 Example 2 was repeated except that the fluoropolymer, the curable component and the curing initiator shown in Table 2 were used.
A solution containing a fluorine-containing curable composition is prepared in the same manner as in -1, coated on a PET film and heat-cured,
A fluorine-containing cured film was prepared. Each measurement was performed on the obtained cured film in the same manner as in Example 1. The results are shown in Table 2.

[0042]

Comparative Example 3 Poly (acrylic acid-3,3,4,4,5,5
5,6,6,7,7,8,8,9,9,10,10,1
10-g of 0-heptadecafluorodecyl) is dissolved in 100 ml of 1,3-bis (trifluoromethyl) benzene, and a thin film coating device (manufactured by Sugiyama Gen Medical Co., Ltd.) is used to obtain a thickness of 500 μm on a PET film. As applied. After drying, each measurement was performed on the obtained fluorine-containing cured coating in the same manner as in Example 1. The results are shown in Table 2.

The abbreviations in Table 2 indicate the following compounds, respectively.

P-F ₁₇ M; poly (methacrylic acid-3,
3,4,4,5,5,6,6,7,7,8,8,9,
9,10,10,10- heptadecafluorodecyl) P-F ₁₇ A; poly (acrylic acid -3,3,4,4,5,
5,6,6,7,7,8,8,9,9,10,10,1
0-heptadecafluorodecyl) P- (St-F ₁₇ M); styrene and methacrylic acid-3,3,3
4,4,5,5,6,6,7,7,8,8,9,9,1
Copolymer of 0,10,10-heptadecafluorodecyl (weight composition ratio 2: 8) TMPTM; trimethylolpropane trimethacrylate TMPTA; trimethylolpropane triacrylate BPO; benzoyl peroxide DAR. 1116; Product name "DAROCUR 1116"
(Merck)

[0045]

[Table 2]

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[Procedure amendment]

[Submission date] March 8, 1993

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0019

[Correction method] Change

[Correction content]

The fluorine-containing cured film of the present invention is obtained by polymerizing and curing the above composition A or composition B,
It has a surface hardness of pencil hardness H or higher and a refractive index of 1.44 or lower. The average molecular weight of the fluorine-containing cured film is preferably 1000 to 300000, and the film thickness is 0.0.
It is preferably 5 to 2000 μm.

Claims (3)

[Claims] 1. A compound represented by the following general formula 1 (wherein X represents a hydrogen atom or a methyl group, and Y represents a C 2-12 fluoroalkyl group having 3 or more fluorine atoms or 4 fluorine atoms).
It shows a C4-C12 fluorocycloalkyl group having the above. ) Fluorine-containing (meth) acrylic acid ester represented by 50) to 50% by weight, and curable component 5 to 50% by weight
A fluorine-containing curable composition comprising: [Chemical 1] 2. The following general formula 2 (wherein X represents a hydrogen atom or a methyl group, and Y represents a C 2-12 fluoroalkyl group having 3 or more fluorine atoms or a fluorine atom 4
It shows a C4-C12 fluorocycloalkyl group having the above. 50-95 containing a fluorine-containing (meth) acrylic acid ester represented by
A fluorine-containing curable composition, characterized by containing 5% by weight and a curable component of 5 to 50% by weight. [Chemical 2] 3. A pencil hardness obtained by polymerizing and curing the fluorine-containing curable composition according to claim 1 or 2 has a surface hardness of H or more and a refractive index of 1.44 or less. Fluorine-containing cured coating.