TW201827443A - Fluorine-containing acrylic compound, method for producing the same, and curable composition and article wherein the article has a water-repellent and oil-repellent surface for antifouling - Google Patents

Abstract

(Rf¹、Rf²係分子量400~20,000的1價或2價的全氟聚醚基，Z¹係可包含O、N及Si的2價烴基，Z²係2價烴基，Q¹係包含(a+b)個以上的Si的(a+b)價的連結基，Q²係包含(b+1)個以上的Si的(b+1)價的連結基，a、b係1~10，c係0、1或2，R係1價烴基，X係CH₂=CR¹-COO-Z³-SiR²R³-O-，R¹係H或1價烴基，R²、R³係1價烴基，Z³係2價烴基)。The object of the present invention is to provide a novel fluorine-containing polyfunctional acrylic compound that can be easily synthesized, a method for producing the same, a curable composition, and an article having a water- and oil-repellent surface. The technical means to solve the problem is a fluorine-containing acrylic compound of the following formula,

(Rf ¹ and Rf ² are monovalent or divalent perfluoropolyether groups with a molecular weight of 400 to 20,000, Z ¹ series can contain O, N and Si divalent hydrocarbon groups, Z ² series are divalent hydrocarbon groups, and Q ¹ series contain (a + b) more than (a + b) -valent linking groups of Si, Q ² includes more than (b + 1) -valent (b + 1) -valent linking groups of Si, and a and b are 1 ~ 10, c series 0, 1 or 2, R series monovalent hydrocarbon group, X series CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, R ¹ series H or monovalent hydrocarbon group, R ² , R ³ series monovalent hydrocarbon group, Z ³ series divalent hydrocarbon group).

Description

Fluorine-containing acrylic compound, manufacturing method thereof, and hardenable composition and article

[0001] The present invention relates to a fluorine-containing polyfunctional acrylic compound and a method for producing the same, a curable composition containing the compound, and an article having a water- and oil-repellent surface formed from a hardened layer of the composition.

[0002] Conventionally, as a means for protecting the surface of a resin molded body or the like, a hard coating process has been widely used. This is because the hardened resin layer (hard coating layer) is hardly formed on the surface of the molded body. As a material constituting the hard coating layer, a thermosetting resin or an ultraviolet or electron-curable resin, or a resin having both functions is used in many cases. [0003] On the other hand, with the expansion of the field of use of resin molded products or the trend of high added value, there is an increasing demand for higher functionalization of the hardened resin layer (hard coating layer), and this is required. One is that it is required to impart antifouling properties to the hard coating layer. This is because the surface of the hard coating layer is provided with properties such as water repellency and oil repellency, so that it is not easily contaminated or can be easily removed even if it is contaminated. [0004] As a method for imparting antifouling properties to a hard coating layer, a method of applying a fluorine-containing antifouling agent to the surface of the hard coating layer once formed and / or fixing the fluorine-containing antifouling agent is generally widely used. The following method has also been studied: adding a fluorine-containing curable component to the hardened resin composition before hardening, and performing hardening by coating to simultaneously harden the formation of a hard coating layer and impart antifouling properties. For example, Japanese Unexamined Patent Publication No. 6-211945 (Patent Document 1) discloses that a fluoroalkyl acrylate is added to an acrylic curable resin composition and cured, thereby producing a hard material that imparts antifouling properties. Coating layer. [0005] In recent years, the requirements for fluorinated acrylic compounds for the purpose of blending into curable resins have become higher. Therefore, new fluorinated polyfunctional acrylic compounds that can be easily synthesized and the improvement of their functions have been strongly demanded. [Prior Art Document] [Patent Document] [0006] [Patent Document 1] Japanese Patent Laid-Open No. 6-211945 [Patent Document 2] Japanese Patent Laid-Open No. 2013-237824 [Patent Document 3] Japanese Patent Laid-Open No. 2010-53114 Gazette [Patent Document 4] JP 2010-138112 [Patent Document 5] JP 2010-285501

[Problems to be Solved by the Invention] [0007] As a fluorine compound capable of imparting antifouling properties to such a curable resin composition, the present inventors have made various developments, for example, Japanese Patent Application Laid-Open No. 2013-237824 Patent Document 2) proposes a method of imparting antifouling properties by blending a fluoroalcohol compound into a thermosetting resin. In addition, the present inventors have proposed, for example, Japanese Patent Laid-Open No. 2010-53114 (Patent Document 3), Japanese Patent Laid-Open No. 2010-138112 (Patent Document 4), and Japanese Patent Laid-Open No. 2010-285501 (Patent Document 5). The photocurable fluorine compound represented. Among these proposals, a method for synthesizing a photocurable fluorine compound is a method in which a fluorine-containing alcohol is reacted with a propylene halide or an acrylic compound having an isocyanate group. [0008] The use of fluorine-containing polyfunctional acrylic compounds for the purpose of blending into curable resins is expanding, and it is also required to optimize the fluorine-containing polyfunctional acrylic compounds for the curable composition to be blended. However, for example, if a fluorine-containing polyfunctional acrylic compound having as many acrylfluorene groups as possible is required, the method of reacting a fluorine-containing alcohol with an acrylfluorene halide or an acrylic compound having an isocyanate group in the aforementioned Patent Document 5 However, there is a disadvantage that the reaction rate of the fluorine-containing alcohol and the acrylic compound having a plurality of isocyanate groups is slow. Further, it is difficult to synthesize and purify an introduction raw material having two or more propylene fluorene groups with respect to one alcohol. [0009] Therefore, when the polyfunctionalization is performed at a stage containing a fluoroalcohol, the compatibility between the polyfunctional alcohol compound having an unsaturated terminal group and the fluoro compound is extremely low, and therefore problems such as poor reaction tend to occur. [0010] The present invention has been made in view of the foregoing circumstances, and an object thereof is to provide a novel fluorine-containing polyfunctional acrylic compound that can be easily synthesized, a method for producing the same, a curable composition containing the compound, and curing of the composition. An object with a water- and oil-repellent surface formed by the material layer. [Means for Solving the Problem] [0011] In order to achieve the above-mentioned object and further research results, the inventors found that the fluorine-containing acrylic compound represented by the following general formula (1) or (2) can meet the above requirements, and thus completed the present invention According to the invention, the fluorine-containing acrylic compound represented by the general formula (1) or (2) is a fluorine-containing reactive silane compound represented by the following general formula (3) or (4), and the following general formula (5) The propylene fluorenyl group-containing silanol compound is obtained by reaction, (In the formula, Rf ¹ is independently a monovalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom, and Rf ^{2 is} based on a carbon number of 1 A bivalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group and an oxygen atom of ~ 6, and Z ¹ is independently a carbon atom having 1 to 20 carbon atoms and may include an oxygen atom, a nitrogen atom, and a silicon atom. A divalent hydrocarbon group may include a cyclic structure on the way, Z ² is independently a divalent hydrocarbon group having 2 to 8 carbon atoms, and Q ¹ is an (a + b) valence containing at least (a + b) silicon atoms. Q ² is independently a (b + 1) -valent linking group containing at least (b + 1) silicon atoms, and can form a cyclic structure. A is 1 to 10 integer, b is independently an integer of lines 1 to 10, c is independently 0, 1 or line 2, Z ¹ (4) is in the formula (3) [] enclosed by a formula or one of Z ¹ And b Z ² systems are all bonded to silicon atoms in the respective Q ¹ or Q ² structures, R is a monovalent hydrocarbon group of 1 to 6 independently, and M is an alkoxy or alkoxyalkyl group) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ¹ , Rf ² , Z ¹ , Z ² , Q ¹ , Q ² , R, R ¹ , R ² , R ³ , a, b, and c are as described above). [0012] Accordingly, the present invention provides the following fluorine-containing acrylic compound, a method for producing the same, a curable composition, and an article. [1] a fluorine-containing acrylic compound represented by the following general formula (1) or (2), (In the formula, Rf ¹ is independently a monovalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom, and Rf ^{2 is} based on a carbon number of 1 A bivalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group and an oxygen atom of ~ 6, and Z ¹ is independently a carbon atom having 1 to 20 carbon atoms and may include an oxygen atom, a nitrogen atom, and a silicon atom. A divalent hydrocarbon group may include a cyclic structure on the way, Z ² is independently a divalent hydrocarbon group having 2 to 8 carbon atoms, and Q ¹ is an (a + b) valence containing at least (a + b) silicon atoms. Q ² is independently a (b + 1) -valent linking group containing at least (b + 1) silicon atoms, and can form a cyclic structure. A is 1 to 10 integer, b is independently an integer of lines 1 to 10, c is independently 0, 1 or line 2, Z ¹ (2) is in the formula (1) [] enclosed by a formula or one of Z ¹ And b Z ² systems are all bonded to the silicon atoms in the respective Q ¹ or Q ² structures, R is independently a monovalent hydrocarbon group of 1 to 6, and X is independently CH ₂ = CR ¹ -COO- The group represented by Z ³ -SiR ² R ³ -O-, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, and R ² and R ³ are each independently 1 to 8 carbon atoms. Valence hydrocarbon group, Z ³ is a divalent hydrocarbon group having 1 to 8 carbon atoms, and may include a cyclic structure in the middle). [2] The fluorine-containing acrylic compound according to [1], wherein Z ² in the general formulae (1) and (2) is -CH ₂ CH ₂ -or -CH ₂ CH ₂ CH _2- . [3] The fluorine-containing acrylic compound according to [1] or [2], wherein X in the general formulae (1) and (2) is a group represented by the following formula, (In the formula, R ² and R ³ are the same as above, and R ⁴ is a hydrogen atom or a methyl group). [4] The fluorine-containing acrylic compound according to any one of [1] to [3], which is represented by the following general formula (6) or (7), (In the formula, Rf ¹ , Rf ² , Z ¹ , Q ¹ , Q ² , a, and b are as described above, and R ⁴ is a hydrogen atom or a methyl group). [5] The fluorine-containing acrylic compound according to any one of [1] to [4], wherein the perfluoropolyether group and the (meth) acrylfluorenyl group are bonded through a connection structure including the following structure , (Wherein Z ² is as described above), and each reactive terminal group [Z ² -SiR _c X _3-c ] _b (Z ² , R, X, b, c is such as The above-mentioned) each has a total of 4 or more (meth) acrylfluorenyl groups. [6] A method for producing a fluorine-containing acrylic compound represented by the following general formula (1) or (2), characterized in that a fluorine-containing reactive silane represented by the following general formula (3) or (4) The compound is reacted with a propenyl group-containing silanol compound represented by the following general formula (5), and the fluorine-containing reactive silane compound represented by the general formula (3) or (4) is the following general formula ( 8) or (9) The fluoropolyether compound having a polyfunctional Si-H group is obtained by performing a hydrosilylation reaction with a terminal unsaturated group-containing reactive silane compound represented by the following general formula (10) , (In the formula, Rf ¹ is independently a monovalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom, and Rf ^{2 is} based on a carbon number of 1 A bivalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group and an oxygen atom of ~ 6, and Z ¹ is independently a carbon atom having 1 to 20 carbon atoms and may include an oxygen atom, a nitrogen atom, and a silicon atom. A divalent hydrocarbon group may include a cyclic structure on the way, Q ¹ is a (a + b) valent linking group containing at least (a + b) silicon atoms, and may form a cyclic structure. Q ² is independently at least A (b + 1) -valent linking group containing (b + 1) silicon atoms and forming a ring structure. A is an integer of 1 to 10, and b is an integer of 1 to 10 independently. A) Z ¹ enclosed by [] or Z ¹ and b H in formula (9) are all bonded to silicon atoms in the respective Q ¹ or Q ² structure) (Where R ⁴ is a hydrogen atom or a methyl group, Z ⁴ is a divalent hydrocarbon group having 1 to 6 carbon atoms, d is 0 or 1, R is independently a monovalent hydrocarbon group of 1 to 6, and M is independently Alkoxy or alkoxyalkyl, c is 0, 1 or 2) (In the formula, Rf ¹ , Rf ² , Z ¹ , Q ¹ , Q ² , R, M, a, b, and c are as described above. Z ² is independently a divalent hydrocarbon group having 2 to 8 carbon atoms. (A Z ¹ enclosed by [] in formula (3) or Z ¹ and b Z ² in formula (4) are all bonded to the silicon atom in the respective Q ¹ or Q ² structure) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ¹ , Rf ² , Z ¹ , Z ² , Q ¹ , Q ² , (R, a, b, c, R ¹ , R ² , R ³ , and Z ³ are the same as described above). [7] A method for producing a fluorine-containing acrylic compound represented by the following general formula (1), characterized in that the fluorine-containing reactive silane compound represented by the following general formula (3) and the following general formula ( 5) Acrylic fluorenyl group-containing silanol compounds represented by reaction are obtained. The fluorine-containing reactive silane compound represented by the general formula (3) is a terminal unsaturated group represented by the following general formula (11). Fluoropolyether compound, and a hydrosilation reaction with a reactive silane compound represented by the following general formula (13), (In the formula, Rf ¹ perfluoro-based carbon atoms by 1 to 6 oxygen atoms and extending the molecular weight of an alkyl composed of a monovalent perfluoropolyether group 400 to 20,000, Z ⁵ having an energy-based end and Si -H group is a monovalent hydrocarbon group having 2 to 20 carbon atoms in the carbon-carbon unsaturated bond, and may include an oxygen atom, a nitrogen atom, and a silicon atom, and may include a cyclic structure in the middle) (In the formula, Q ¹ is a (a + b) valent linking group containing at least (a + b) silicon atoms, and can form a ring structure. Z ² is independently a divalent one having 2 to 8 carbon atoms. Hydrocarbyl, R is independently a monovalent hydrocarbon group of 1 to 6, M is independently an alkoxy or alkoxyalkyl group, a is an integer of 1 to 10, b is an integer of 1 to 10, and c is 0 or 1 Or 2, a H and b Z ² are all bonded to the Si atom in Q ¹ ) (In the formula, Rf ¹ , Z ² , Q ¹ , R, M, a, b, and c are the same as described above. Z ¹ is independently 2 of 2 to 20 carbon atoms which may include an oxygen atom, a nitrogen atom, and a silicon atom. Valent hydrocarbon groups may include a cyclic structure on the way, and all of the a Z ¹ and b Z ² systems enclosed by [] are bonded to the silicon atom in the Q ¹ structure) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ¹ , Z ¹ , Z ² , Q ¹ , R, a, b, c, R ¹ , R ² , R ³ , and Z ³ are the same as described above). [8] A method for producing a fluorine-containing acrylic compound represented by the following general formula (2), characterized in that the fluorine-containing reactive silane compound represented by the following general formula (4) and the following general formula ( 5) Acrylic fluorenyl group-containing silanol compounds represented by reaction are obtained. The fluorine-containing reactive silane compound represented by the general formula (4) is a terminal unsaturated group represented by the following general formula (12). The fluoropolyether compound is obtained by performing a hydrosilylation reaction with a reactive silane compound represented by the following general formula (14), (In the formula, Rf ² is a divalent perfluoropolyether group having a molecular weight of 400 to 20,000, which is composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom. Z ⁵ is independently a terminal having one energy. A monovalent hydrocarbon group having 2 to 20 carbon atoms in the carbon-carbon unsaturated bond that undergoes an addition reaction with the Si-H group and may include an oxygen atom, a nitrogen atom, and a silicon atom, and may include a cyclic structure in the middle) (In the formula, Q ² is a (b + 1) -valent linking group containing at least (b + 1) silicon atoms, and can form a cyclic structure. Z ² is independently a bivalent having 2 to 8 carbon atoms. Hydrocarbyl, R is independently a monovalent hydrocarbon group of 1 to 6, M is independently an alkoxy or alkoxyalkyl group, b is an integer of 1 to 10, c is 0, 1, or 2, H and b (Z ² is all bonded to Si atoms in Q ² ) (In the formula, Rf ² , Z ² , Q ² , R, M, b, and c are the same as above, and Z ¹ is independently a divalent one having 1 to 20 carbon atoms and which may include an oxygen atom, a nitrogen atom, and a silicon atom. A hydrocarbon group may include a cyclic structure on the way, and all Z ¹ and b Z ² systems are bonded to silicon atoms in the Q ² structure) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ² , Z ¹ , Z ² , Q ² , R, b, c, (R ¹ , R ² , R ³ , and Z ³ are the same as described above). [9] A curable composition comprising the fluorine-containing acrylic compound according to any one of [1] to [5]. [10] The curable composition according to [9], wherein the refractive index of the cured product is 1.4 or less. [11] An article having a hardened material layer having a hardenable composition according to [9] or [10] on its surface. [12] The article according to [11], wherein the hardened layer has a water-repellent and oil-repellent surface having a contact angle of water of 100 ° or more and a contact angle of oleic acid of 60 ° or more. [Effects of the Invention] [0013] The fluorine-containing acrylic compound of the present invention exhibits stable solubility, does not impair the characteristics of fluorine, and has a large number of (meth) acrylfluorenyl groups for terminal groups, and is therefore suitable for use. Antifouling additives for imparting antifouling properties to UV-curable hard coating agents, UV-curable coatings, UV-curable resins, UV-curable anti-reflective coating compositions, and the like.

[Best Mode for Carrying Out the Invention] The fluorinated acrylic compound of the present invention is one represented by the following general formula (1) or (2). The fluorinated acrylic compound of the present invention, the perfluoropolyether group and the (meth) acryl group are bonded through a connection structure including a structure described below, (Where, Z ² And Z of equations (1) and (2) ² The same), and each reactive terminal group connected to the fluoropolyether chain, that is, [Z in the above formulas (1) and (2) ² -SiR _c X _3-c ] _b Each has a total of 4 or more (meth) acrylfluorenyl groups, especially -Si-O-Si- [Z ² -SiR _c X _3-c ] _b Medium, [Z ² -SiR _c X _3-c ] _b Those having a total of 4 (meth) acrylfluorenyl groups are more preferable. [0016] In the formulae (1) and (2), Rf ¹ It is a monovalent perfluoropolyether group with a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom. Rf ² It is a divalent perfluoropolyether group with a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom. Rf ¹ Rf ² In particular, it is suitable to use a perfluorooxyalkylene structure having a carbon number of 1 to 3 as a main repeating unit. Such a structural system may be any one kind of homopolymer or a random or block polymer formed by a plurality of structures. [0017] As Rf having such a structure ¹ A suitable example is as follows. (In the formula, p is an integer of 0 to 400, preferably an integer of 0 to 200, q is an integer of 0 to 170, preferably an integer of 0 to 100, and p + q is an integer of 2 to 400, preferably an integer of 3 to 300. ) (Where r is 1 to 120, preferably an integer from 1 to 80) (In the formula, s is an integer of 1 to 120, preferably an integer of 1 to 80.) [0018] Also, as Rf ² A suitable example is as follows. (In the formula, p is an integer of 0 to 400, preferably an integer of 0 to 200, q is an integer of 0 to 170, preferably an integer of 0 to 100, and p + q is an integer of 2 to 400, preferably an integer of 3 to 300. ) [0019] (Wherein t + u is 2 to 120, preferably an integer of 4 to 100) [0020] Rf ¹ Rf ² The molecular weight of the group corresponds to the number-average molecular weight of the structural part, which is 400 to 20,000, preferably in the range of 800 to 10,000, and the molecular weight distribution is not particularly limited. In the present invention, the molecular weight is determined by ¹ H-NMR and ¹⁹ The number average molecular weight calculated by the ratio of the terminal structure to the main chain structure of F-NMR. [0021] In the formulae (1) and (2), Rf ¹ And Rf ² The bonds are all bonded to Z ¹ . Z ¹ It is a divalent hydrocarbon group having 1 to 20 carbon atoms, preferably 2 to 16 carbon atoms, which may contain an oxygen atom, a nitrogen atom, and a silicon atom, and may include a cyclic structure in the middle. As Z ¹ Particularly preferred structures include the following. [0022] In the above formulas (1) and (2), a and b are each independently an integer of 1 to 10, preferably an integer of 1 to 8, and more preferably an integer of 1 to 4. [0023] In the above formula (1), Q ¹ It is a (a + b) -valent linking group containing at least (a + b) silicon atoms, and can form a ring structure. As such a Q ¹ Preferred examples include a siloxane structure having (a + b) Si atoms, a non-substituted or halogen-substituted silalkylene structure, a silylene structure, or a (A + b) -valent linking group formed by a combination of these two or more kinds. As a particularly preferable structure, the following structure can be shown specifically. [0024] However, a and b are the same as a and b in the formula (1), and are each independently an integer of 1 to 10, preferably an integer of 1 to 8, and more preferably an integer of 1 to 4. e is an integer of 1 to 5, preferably an integer of 3 to 5. The arrangement of each unit is random, the bond system of each unit such as (a + b) units, and the Z of a unit enclosed by [] ¹ And b z ² Any of the base bonds. [0025] [0026] Here, examples of the T-group (a + b) -valent linking group are as follows. [0027] In the above formula (2), Q ² It is a (b + 1) -valent linking group containing at least (b + 1) silicon atoms and can form a ring structure. As such a Q ² Preferred examples include a siloxane structure having (b + 1) Si atoms, a non-substituted or halogen-substituted silyl structure, a silyl structure, or two or more of these. (B + 1) -valent linking group formed by the combination of. As a particularly preferable structure, the following structure can be shown specifically. [0028] However, b is the same as b in the above formula (2), and is independently an integer of 1 to 10, preferably an integer of 1 to 8, and more preferably an integer of 1 to 4. e 'is an integer of 1 to 5, preferably an integer of 1 to 3. The arrangement of each unit is random, and (b + 1) of each unit, etc. ¹ And b's Z enclosed by [] ² Any of the base bonds. [0029] [0030] Here, T ′ is a (b + 1) -valent linking group, and examples thereof include the following. [0031] In the formulae (1) and (2), R is independently a monovalent hydrocarbon group of 1 to 6, preferably 1 to 4. Specific examples of the monovalent hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, and hexyl, Cycloalkyl such as cyclohexyl, alkenyl such as vinyl, allyl, and propenyl, phenyl, and the like are preferably methyl. In the formulae (1) and (2), c is independently 0, 1 or 2, preferably 0 or 1, and still more preferably 0. However, the total of R and X bonded to one silicon atom is 3. [0032] In the formulae (1) and (2), Z ² The divalent hydrocarbon group having 2 to 8 carbon atoms may include a cyclic structure in the middle. As Z ² As a preferable structure, the following can be mentioned. Of these Is better. [0033] In the above formulas (1) and (2), X is independently represented by the following formula. Here, R ¹ Is independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, preferably 1 to 6, R ² And R ³ A monovalent hydrocarbon group having 1 to 8 carbon atoms, and preferably 1 to 6 carbon atoms. Specific examples of such monovalent hydrocarbon groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, and octyl groups. Alkyl such as cyclohexyl, cycloalkyl such as cyclohexyl, alkenyl such as vinyl, allyl, propenyl, aryl such as phenyl, tolyl, xylyl, benzyl, phenylethyl, etc. Aralkyl, etc. As R ¹ Suitable for hydrogen atom and methyl group, as R ² And R ³ Methyl is particularly suitable. Again, Z ³ It is independently a divalent hydrocarbon group having 1 to 8 carbon atoms, and may include a cyclic structure in the middle. Particularly preferred is the structure described below. [0034] X is preferably a group represented by the following formula. (Where, R ² , R ³ Is the same as above, R ⁴ (A hydrogen atom or a methyl group) [0035] As the fluorine-containing acrylic compound represented by the formulae (1) and (2), those represented by the following general formulae (6) and (7) are preferred. (Where, Rf ¹ Rf ² , Q ¹ , Q ² ,Z ¹ , A, b, R ⁴ (As described above) [0036] As the fluorine-containing acrylic compound represented by the formulae (1) and (2), more specific examples are as follows. (Where Rf 'is -CF ₂ O (CF ₂ O) _p1 (CF ₂ CF ₂ O) _q1 CF ₂ -, And satisfy q1 + p1 = 5 ~ 80, r1 is an integer of 2-100, preferably an integer of 2-50, and n is independently 2 or 3). [0037] The synthesis method of the fluorine-containing acrylic compound represented by the general formula (1) or (2) is not particularly limited, but for example, the fluorine-containing acrylic compound represented by the following general formula (3) or (4) is used. A reactive silane compound can be obtained by reacting with a propylene fluorenyl group-containing silane alcohol compound represented by the following general formula (5). . [0038] In the formulae (3) to (5), Rf ¹ Rf ² ,Z ¹ ,Z ² ,Z ³ , Q ¹ , Q ² , R, M, R ¹ , R ² , R ³ , A, b, and c are as described above. Z of a number enclosed by [] in formula (3) ¹ Or Z in equation (4) ¹ And b z ² All bound to separate Q ¹ Or Q ² Silicon atoms in construction. [0039] M is alkoxy or alkoxyalkyl. Examples of M include alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, and isopropoxy, methoxymethyl, methoxyethyl, and ethoxymethyl. And alkoxyalkyl groups having 2 to 4 carbon atoms, such as an ethoxy group and an ethoxyethyl group. Among these, a methoxy group, an ethoxy group, and a methoxymethyl group are particularly suitable. [0040] Here, examples of the fluorine-containing reactive silane compound represented by the formulae (3) and (4) are shown below. (In the formula, r1 and Rf ′ are the same as described above). [0041] Examples of the propylene fluorenyl group-containing silanol compound represented by the formula (5) include the following. [0042] The reaction of the fluorine-containing reactive silane compound represented by the formula (3) or (4) with the acrylfluorenyl group-containing silanol compound represented by the formula (5) may be performed with a catalyst as needed. Or solvent together. The reaction system can be carried out at a temperature of 0 to 120 ° C, preferably 10 to 70 ° C, for 1 minute to 300 hours, preferably 30 minutes to 72 hours. If the reaction temperature is too low, the reaction rate may become too slow. If the reaction temperature is too high, it may cause polymerization of the propylene fluorenyl group as a side reaction, or the propylene fluorene containing the formula (5). The possibility of dehydration condensation of silanol compounds based on each other. [0043] In the reaction between the fluorine-containing reactive silane compound represented by formula (3) or (4) and the propylene fluorenyl group-containing silanol compound represented by formula (5), the propylene fluorene containing fluorene represented by formula (5) The amount of the silanol compound based on the group is 0.95 to 2 times the mole of the total mole of M contained in the fluorine-containing reactive silane compound represented by the formula (3) or (4) present in the reaction system. It is better to use 1 to 1.5 times mole. [0044] In this reaction, an appropriate catalyst may be added in order to increase the reaction speed. For example, when M is an alkoxy group, examples of the catalyst include dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctoate, dioctyltin diacetate, dioctyltin dilaurate, and dioctanoic acid. Alkyl tin ester compounds such as dioctyltin, stannous dioctoate, titanium tetraisopropoxide, titanium n-butoxy, titanium tetra-2- ethylhexoxide, Titanate or titanium chelate compounds such as dipropoxy bis (acetamidinepyruvate) titanium, titanium isopropoxyoctanediol, zirconium tetraacetammonium pyruvate, zirconium tributoxymonoacetamylpyruvate , Zirconium monobutoxyacetamidine pyruvate bis (ethylacetamidineacetate) zirconium, Dibutoxybis (ethylacetammonium acetate) zirconium, zirconium tetraacetamidine pyruvate, zirconium chelate compounds, magnesium hydroxide, Alkaline earth hydroxides such as calcium hydroxide, strontium hydroxide, and barium hydroxide. These are not limited to one type, and can be used as a mixture of two or more types, but it is particularly preferable to use a titanium compound, a zirconium compound, or an alkaline earth hydroxide having a low impact on the environment. By adding these catalysts in an amount of 0.01 to 10% by mass, preferably 0.01 to 5% by mass relative to the total mass of the reactants, the reaction speed can be increased. [0045] The above reaction can be diluted and reacted with a suitable solvent as required. As such a solvent, any solvent that does not directly react with each reactive group of the compounds of the formulae (3), (4), and (5) may be used without particular limitation. Specific examples include Hydrocarbon solvents such as toluene, xylene, isooctane, ether solvents such as tetrahydrofuran, diisopropyl ether, and dibutyl ether, acetone, methyl ethyl ketone, methyl butyl ketone, and methyl isobutyl Ketone solvents such as ketones and cyclohexanone; fluorine-modified aromatic hydrocarbon solvents such as m-xylenehexafluoride and benzotrifluoride; fluorine such as methyl perfluorobutyl ether Modified ether solvents. This solvent can be removed after the reaction by a well-known method such as distillation under reduced pressure, or it can be used directly as a dilute solution for the intended purpose. When a solvent is used, the amount used is preferably 0.1 to 1,000 parts by mass, and more preferably 20 to 500 parts by mass based on 100 parts by mass of the compound of the formulae (3), (4), and (5). . When the value is larger than this value, the concentration of the reaction system may be excessively reduced, and the reaction speed may be significantly reduced. [0046] During the reaction, a polymerization inhibitor may be added as needed. It does not specifically limit as a polymerization inhibitor, It can use what is generally used as a polymerization inhibitor of an acrylic compound. Specific examples include hydroquinone, hydroquinone monomethyl ether, 4-tert-butylcatechol, and dibutylhydroxytoluene. [0047] After completion of the reaction, if necessary, the unreacted propylene fluorenyl group-containing silanol compound represented by formula (5) and the reaction are removed by methods such as distillation, adsorption, reprecipitation, filtration, and washing. A solvent and the like to obtain a fluorine-containing acrylic compound represented by the formula (1) or (2) of the present invention. [0048] The synthesis method of the fluorine-containing reactive silane compound represented by the general formula (3) or (4) is not particularly limited, but as one embodiment of the present invention, first, the following general A hydrosilylation reaction with a polyfunctional Si-H group-containing fluoropolyether compound represented by the formula (8) or (9) and a reactive silane compound containing a terminal unsaturated group represented by the following general formula (10) (hydrosilylation reaction). (Where, Q ¹ , Q ² Rf ¹ Rf ² ,Z ¹ , A, and b are the Z of a number enclosed by [] in formula (8) as described above. ¹ Or Z in equation (9) ¹ And b hydrogen atoms (H) are all bonded to the respective Q ¹ Or Q ² (Silicon atoms in structure) (Where, R ⁴ , R, M, c are as described above, Z ⁴ It is a divalent hydrocarbon group having 1 to 6 carbon atoms, and d is 0 or 1). [0049] Here, examples of the fluoropolyether compound having a polyfunctional Si—H group represented by the formulae (8) and (9) are as follows. (In the formula, Rf ′ and r1 are the same as those described above.) [0050] Examples of the reactive unsaturated silane compound containing a terminal unsaturated group represented by the above formula (10) include the following. [0051] Among them, the following are particularly suitable. [0052] The fluoropolyether compound having a polyfunctional Si-H group represented by the formulae (8) and (9), and a reactive silane compound containing a terminal unsaturated group represented by the formula (10) are based on These are mixed and stirred, and in the presence of a platinum group metal-based addition reaction catalyst, at a reaction temperature of 50 to 150 ° C, preferably 60 to 120 ° C, for 1 minute to 72 hours, especially 5 minutes. ~ 12 hours reaction is appropriate. If the reaction temperature is too low, the reaction may be stopped in a state where the reaction cannot be fully performed. If it is too high, the temperature may rise due to the heat of the hydrosilylation reaction and the reaction cannot be controlled, causing bumping. Or the decomposition of raw materials. [0053] At this time, the fluoropolyether compound having a polyfunctional Si-H group represented by the formula (8) or (9) and the reactive unsaturated silane compound containing a terminal unsaturated group represented by the formula (10) are fed. The ratio of the molar ratio of H to the total moles of H enclosed by [] of the fluoropolyether compound having a polyfunctional Si-H group represented by formula (8) or (9) is expressed by formula (10). The terminal unsaturated group-containing reactive silane compound has an unsaturated group of 0.8 to 5 times mole, and it is particularly preferable to use 0.1 to 2 times mole for reaction. If the terminal unsaturated group-containing reactive silane compound represented by formula (10) is too small compared to the above value, the fluoropolyether compound having a polyfunctional Si-H group represented by (8) and (9) will remain Many Si-H groups may be difficult to obtain the intended effect. If the value is too large, the uniformity of the reaction solution will decrease and the reaction rate will become unstable. After the reaction, if a reactive silane compound containing a terminal unsaturated group represented by formula (10) is removed, In this case, it is necessary to perform conditions such as heating, decompression, and extraction more strictly in accordance with the increased amount of the remaining unreacted components. [0054] As the addition reaction catalyst system, a compound containing a platinum group metal such as platinum, rhodium, or palladium can be used. Among them, a compound containing platinum is preferable, and hexachloroplatinum (IV) acid hexahydrate, platinum carbonyl vinylmethyl complex, platinum-divinyltetramethyldisilaxane complex, Platinum-cyclovinylmethylsiloxanes complexes, platinum-octaldehyde / octanol complexes, complexes of chloroplatinic acid with olefins, aldehydes, vinylsiloxanes or acetylene alcohols, or Platinum carried by activated carbon. The blending amount of the addition reaction catalyst is preferably 0.1 to 5,000 mass ppm relative to the fluoropolyether compound having a polyfunctional Si-H group represented by formula (8) or (9). , And preferably 1 to 1,000 mass ppm. [0055] The above-mentioned addition reaction can be carried out even in the absence of a solvent, and the solvent can be used for dilution if necessary. In this case, a generally used organic solvent such as toluene, xylene, and isooctane can be used as the diluent solvent. As such an organic solvent, it is preferred that the boiling point is higher than the intended reaction temperature without hindering the reaction, and the fluorine-containing reactive silane compound represented by the formula (3) or (4) produced after the reaction is subjected to the above reaction. Soluble in temperature. For example, a partially modified fluorine-containing solvent such as a fluorine-modified aromatic hydrocarbon solvent such as hexafluorom-xylene, trifluorotoluene, or a fluorine-modified ether solvent such as methyl perfluorobutyl ether is preferable, and particularly Hexafluorom-xylene is preferred. When a solvent is used, the solvent is preferably used in an amount of 5 to 2,000 parts by mass relative to 100 parts by mass of the fluoropolyether compound having a polyfunctional Si-H group represented by formula (8) or (9). It is preferably 50 to 500 parts by mass. If it is less than the above value, the dilution effect by the solvent is weak; when it is more than the above value, the dilution degree becomes too high and the reaction speed may be reduced. [0056] After the reaction is completed, the unreacted terminal unsaturated group-containing reactive silane compound or dilute solvent represented by the formula (10) is removed by a known method such as distillation under reduced pressure, extraction, and adsorption to It is preferable, but the reaction mixture containing these can also be used directly in the next reaction. [0057] As another synthetic route of the fluorine-containing reactive silane compound represented by the formulae (3) and (4) in the present invention, as another form of the embodiment of the present invention, the following can be achieved by making A fluoropolyether compound having a terminal unsaturated group represented by the general formula (11) and a reactive silane having at least one Si-H group and at least one hydrolyzable silane group represented by the following general formula (13) A compound, or a fluoropolyether compound having a terminal unsaturated group represented by the following general formula (12), and at least one Si-H group and at least one hydrolyzable silane group represented by the following general formula (14) Obtained by reacting a reactive silane compound. (Where, Rf ¹ Rf ² , Q ¹ , Q ² ,Z ² , R, M, a, b, c are as described above, Z ⁵ It is independently a monovalent hydrocarbon group having 2 to 20 carbon atoms having one carbon-carbon unsaturated bond capable of undergoing addition reaction with Si-H group at the end, and may include an oxygen atom, a nitrogen atom, and a silicon atom. Ring structure, H of a number enclosed by [] in Formula (13) or H and b of Z in Formula (14) ² All bound to separate Q ¹ Or Q ² Silicon atoms in the structure). [0058] Here, as Z in the general formulae (11) and (12) ⁵ Specifically, the following structures can be cited. [0059] Here, examples of the fluoropolyether compound having a terminal unsaturated group represented by the formulae (11) and (12) are as follows. (However, r1 and Rf 'are as described above). [0060] Examples of the reactive silane compound having at least one Si-H group and at least one hydrolyzable silane group represented by the formulae (13) and (14) include the following. A fluoropolyether compound having a terminal unsaturated group represented by formula (11) and a reactive silane compound represented by formula (13), or a fluoropolyether having a terminal unsaturated group represented by formula (12) The reaction between the compound and the reactive silane compound represented by the formula (14) is to mix these, and in the presence of a platinum group metal-based addition reaction catalyst at a reaction temperature of 50 to 150 ° C, preferably The reaction is preferably performed at 60 to 120 ° C for 1 minute to 48 hours, especially 10 minutes to 12 hours. If the reaction temperature is too low, the reaction may be stopped in a state where the reaction cannot be fully performed. If it is too high, the temperature may rise due to the heat of the hydrosilylation reaction and the reaction cannot be controlled, causing bumping. Or the decomposition of raw materials. In the reaction, all the raw materials may be mixed beforehand, or any raw materials may be added or dropped afterwards. [0062] At this time, the reaction ratio of the fluoropolyether compound having a terminal unsaturated group represented by formula (11) or (12) to the reactive silane compound represented by formula (13) or (14) is relative to The total number of moles of the terminal unsaturated groups in formula (11) or (12), the total amount of H enclosed by [] in formula (13), or H in formula (14) is 0.9 to 2 times moles, In particular, it is suitable to use and react so as to be 1 to 1.05 times mole. It is preferable that H is enclosed by [] in the formula (13) or H in the formula (14). [0063] As the addition reaction catalyst system, a compound containing a platinum group metal such as platinum, rhodium, or palladium can be used. Among them, a compound containing platinum is preferable, and hexachloroplatinum (IV) acid hexahydrate, platinum carbonyl vinylmethyl complex, platinum-divinyltetramethyldisilaxane complex, Platinum-cyclovinylmethylsiloxane complex, platinum-octanal / octanol complex, or platinum supported on activated carbon. The blending amount of the addition reaction catalyst is preferably 0.1 to 5,000 mass ppm relative to the fluoropolyether compound having a terminal unsaturated group represented by formula (11) or (12). It is preferably 1 to 1,000 mass ppm. [0064] The above-mentioned addition reaction can be carried out even in the absence of a solvent, and the solvent can be used for dilution if necessary. In this case, a generally used organic solvent such as toluene, xylene, and isooctane can be used as the diluent solvent. However, the reaction temperature is higher than the boiling point and does not hinder the reaction. Formula (3) generated after the reaction Or it is preferable that the fluorine-containing reactive silane compound represented by (4) is soluble at the above-mentioned reaction temperature. As such a solvent, for example, fluorine-modified aromatic hydrocarbon solvents such as hexafluorom-xylene and trifluorotoluene, and fluorine-modified ether solvents such as methyl perfluorobutyl ether are partially modified by fluorine. Solvents are preferred, and hexafluorom-xylene is particularly preferred. When a solvent is used, the solvent is preferably used in an amount of 5 to 2,000 parts by mass relative to 100 parts by mass of the fluoropolyether compound having a terminal unsaturated group represented by formula (11) or (12). It is 50 to 500 parts by mass. If it is less than the above value, the dilution effect by the solvent is weak; when it is more than the above value, the dilution degree becomes too high and the reaction speed may be reduced. [0065] After the reaction is completed, it is preferable to remove the unreacted reactive silane compounds represented by the formulae (13) and (14) by a known method such as distillation under reduced pressure, extraction, and adsorption, but also The reaction mixture containing these can be used directly in the next reaction. [0066] Using the fluorine-containing reactive silane compounds represented by the formulas (3) and (4) obtained as described above, these are combined with the propylene fluorenyl group represented by the formula (5) by the aforementioned method. By reacting the silanol compounds, the fluorine-containing acrylic compounds represented by the formulae (1) and (2) of the present invention can be obtained. [0067] Another embodiment of the present invention is a curable composition containing a fluorine-containing acrylic compound represented by formulas (1) and (2) obtained as described above. As the curable composition, in particular, It is suitable to perform hardening by active energy rays. The fluorine-containing acrylic compound [hereinafter collectively referred to as the fluorine-containing acrylic compound (A)] represented by the formulae (1) and (2) can be hardened separately, but it can be hardened with other active energy rays, for example. When the component (B) is blended, excellent antifouling properties due to the component (A) can be imparted to the surface while maintaining the characteristics of the hardened product as the component (B) such as hardness. [0068] The component (A) may be one or two or more kinds of the fluorine-containing acrylic compound represented by the formula (1), or one or two kinds of the fluorine-containing acrylic compound represented by the formula (2). The above may be a mixture of the fluorine-containing acrylic compound represented by the formula (1) and the fluorine-containing acrylic compound represented by the formula (2). [0069] The active energy ray-curable component that can be suitably used for the component (B) other than the component (A) in the present invention is not limited as long as it can be mixed and cured with the component (A). Any one can be used, but Acrylates are particularly preferred. Examples include, for example, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and ethylene glycol di (meth) ) Acrylate, ethylene isocyanate modified di (meth) acrylate, isotricyanate EO modified tri (meth) acrylate, trimethylolpropane tri (meth) acrylic acid Ester, pentaerythritol tri (meth) acrylate, glycerol tri (meth) acrylate, gins (meth) acryloxyethyl phosphate, hydrogen phthalate- (2,2,2-tri -(Meth) acryloxymethyl) ethyl ester, glycerol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pyrenetrimethylolpropane tetra (meth) acrylate, di 2 to 6-functional (meth) acrylic compounds such as pentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, sorbitol hexa (meth) acrylate, etc .; ) Acrylic acid epoxy esters obtained by adding acrylic acid to ethylene oxide, propylene oxide, epichlorohydrin, fatty acids, alkyl modified products, and epoxy resins; and side chains of acrylic copolymers A copolymer obtained by introducing a (meth) acrylfluorenyl group, and the like. [0070] Also, urethane acrylates can be used; those obtained by reacting a (meth) acrylate having a hydroxyl group with a polyisocyanate; and a (meth) acrylate having a hydroxyl group and a polyisocyanate with A polyester obtained by reacting a terminal diol with a polyester; a polyisocyanate obtained by reacting an excess of a diisocyanate with a polyol, and a reaction with a (meth) acrylate having a hydroxyl group. Among these, a (meth) acrylate having a hydroxyl group selected from 2-hydroxyethyl (meth) acrylate, 2-hydroxy-3-propenyloxypropyl methacrylate, and pentaerythritol triacrylate is particularly preferred. ; With hexamethylene diisocyanate, isophorone diisocyanate, toluene diisocyanate, lysine diisocyanate, norbornane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, Methylbis (4-cyclohexyl isocyanate), 2-methyl-1,3-diisocyanate cyclohexane, 2-methyl-1,5-diisocyanate cyclohexane, and diphenyl Urethane acrylates obtained by reacting a polyisocyanate selected from methane diisocyanates are preferred. [0071] The component (B) may be used alone or in combination of two or more. In order to adjust the physical properties of the composition, monofunctional acrylates may be blended. In addition, as the component (B), the following compounds may be included: the compound is acryl-containing fluorene represented by formula (5) remaining during the synthesis of the fluorine-containing acrylic compound represented by formulas (1) and (2) A silanol compound having a basic structure, or a compound having a structure represented by the following formula (15), and the compound having a structure represented by the formula (15) is a silyl alcohol compound 2 containing acrylhydrazone according to formula (5) By-products from molecular dehydration reactions. (Where, R ¹ , R ² , R ³ ,Z ³ (As above). [0072] The curable composition of the present invention can be made into a curable composition that is cured by ultraviolet rays by containing a photopolymerization initiator as the component (C). The photopolymerization initiator of the component (C) is not particularly limited as long as it can cure an acrylic compound by ultraviolet irradiation, but preferred examples include acetophenone, benzophenone, and 2,2- Dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl-one, 2-hydroxy-2-methyl-1-phenyl-propane-1-one, 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propane-1-one, 2-methyl-1- (4-methylthiophenyl) ) -2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 2- (dimethylamine ) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, 2,4,6-trimethylbenzoyl Fluorenyl-diphenyl-phosphine oxide, bis (2,4,6-trimethylbenzylidene) -phenylphosphine oxide, 1,2-octanedione-1- [4- (phenylthio) -2- (o-benzidine oxime)], ethyl ketone-1- [9-ethyl-6- (2-methylbenzyl) -9H-carbazol-3-yl] -1- ( O-acetamoxime), 2-hydroxy-1-fluorene 4- [4- (2-hydroxy-2-methyl-propanyl) -benzyl] phenylphosphonium-2-methyl-propane-1- Ketones can be used alone or in combination of two or more. [0073] The hardenable composition according to one embodiment of the present invention contains the component (A) and imparts water-repellent and oil-repellent properties to the hardened surface as its essence. Therefore, the blending amount of each component should be in accordance with the expectation. The water repellency, oil repellency, composition solubility, coating conditions, hardening conditions, hardness of the obtained article, etc. may be appropriately determined, and may be used: (A) component, (A) component, and (C) component alone , (A) component and (B) component, (A) component and (B) component and (C) component, and any combination of these with other additives mentioned later to be added as needed, but it is suitable to include Compositions of (A) component and (B) component and (C) component. At this time, the blending ratio of the (B) component and the (C) component with respect to the (A) component is not particularly limited. For example, the blending amount of the (B) component is preferably 0.1 with respect to 1 part by mass of the (A) component. ~ 10,000 parts by mass, more preferably 1 ~ 1,000 parts by mass, and particularly preferably 5 ~ 200 parts by mass. Furthermore, when the total amount of (A) component and (B) component is 100 mass parts, the compounding quantity of (C) component becomes like this. Preferably it is 0.1-10 mass parts, Especially preferably, it is 0.5-5 mass parts. [0074] Various types of acrylic compositions and hard coating agents obtained by blending the component (C) with the component (B) are already commercially available from various companies. The curable composition of the present invention can be obtained by adding the component (A) to such a commercially available product. Commercially available hard coating agents include, for example, Arakawa Chemical Industry Co., Ltd. "Beam set", Ohashi Chemical Industry Co., Ltd. "Ubic", Origin Electric Co., Ltd. "UV Coat", Cashew Co., Ltd. "Cashew" UV '', JSR (share) `` DeSolite '', Dainichi Chemical Industries (share) `` Seikabeam '', Japan Synthetic Chemical (share) `` Purple Light '', Fujikura Kasei (share) `` Fujihard '', Mitsubishi Rayon (share) `` Diabeam, Takeyo Paint Co., Ltd. "ULTRA VIN", DIC (Stock) "UNIDIC", etc. Moreover, even when using such a commercially available composition, you may add (B) component and (C) component as needed. [Other additives] In the hardening composition of the present invention, an organic solvent, a polymerization inhibitor, an antistatic agent, an antifoaming agent, a viscosity adjusting agent, a light resistance stabilizer, a heat resistance stabilizer, and an antioxidant may be prepared according to the purpose. , Surfactants, colorants, and fillers. In addition, even in the case where a commercially available hard coating agent is used as described above, an organic solvent, a polymerization inhibitor, an antistatic agent, an antifoaming agent, a viscosity adjusting agent, a light resistance stabilizer, and a heat resistance stabilizer can be prepared according to the purpose. , Antioxidants, surfactants, colorants, and fillers. [0076] Examples of the organic solvent include 1-propanol, 2-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, diacetone alcohol, and the like; methylpropyl Ketones such as ketones, diethyl ketones, methyl ethyl ketones, methyl isobutyl ketones (MIBK), cyclohexanone; dipropyl ether, dibutyl ether, anisole, dioxane, ethyl Ethers such as glycol monoethyl ether, glycol monobutyl ether, propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate; ethyl acetate, propyl acetate, butyl acetate, acetic acid Ester such as cyclohexyl ester. These organic solvents may be used alone or in combination of two or more. The use amount of the organic solvent is not particularly limited, but is preferably 50 to 10,000 parts by mass, and more preferably 100 to 1,000 parts by mass, with respect to 100 parts by mass of the total of the components (A) to (C). [0077] The polymerization inhibitor, antistatic agent, antifoaming agent, viscosity adjuster, light resistance stabilizer, heat resistance stabilizer, antioxidant, surfactant, colorant, and filler are not particularly limited. A well-known thing can be used in the range which does not impair the objective of this invention. [0078] The method for curing the curable composition of the present invention is not particularly limited, and the composition of the component (A) alone can be diluted with an appropriate solvent, and the coater can use an active energy ray such as an electron beam to make the composition Although it hardens | cures, when it contains a photopolymerization initiator of (C) component, it can harden by ultraviolet rays. In the case of hardening by ultraviolet rays, it is also possible to irradiate ultraviolet rays in the air, but in order to prevent the hardening caused by oxygen, it is better to suppress the oxygen concentration to less than 5,000 ppm, such as nitrogen, carbon dioxide, argon, etc. It is particularly good to harden it under an inert gas environment. In addition, when used as a coating of a base material such as a film or a coating for various articles, the component (B) or other additives can be freely blended in accordance with any desired characteristics of the purpose. [0079] As a general use form of the curable composition of the present invention, it can be applied to various resin film substrates. Examples of such a resin film include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyethylene, polypropylene, selovan, and diethylfluorene fiber. Cellulose, triethyl cellulose, ethyl cellulose butyrate, cellulose acetate propionate, cyclic olefin polymer, cyclic olefin copolymer, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, ethylene-acetic acid Vinyl ester copolymers, polystyrene, polycarbonate, polymethylpentene, polyfluorene, polyetheretherketone, polyetherfluorene, polyetherimine, polyimide, fluororesin, nylon, acrylic resin And other resin films. In addition, a structure in which an adhesive is applied to a surface opposite to the application and formation of the curable composition layer of the film substrate may be adopted, and a release film for protecting the adhesive may be disposed. [0080] The film substrate may be a substrate made of only the resin films mentioned above. However, in order to improve the adhesion with the curable composition of the present invention, a base may be provided on the resin film. Lacquered film substrate. Examples of the primer coating layer include a polyester resin, a urethane resin, and an acrylic resin. In addition, for the purpose of improving the adhesiveness with the hardenable composition of the present invention, the surface of the resin film may be subjected to a roughening treatment on the surface by a sandblasting method, a solvent treatment method, or the like, a corona discharge treatment, or a chromate treatment , Flame treatment, hot air treatment, ozone / ultraviolet irradiation treatment, oxidation treatment, and the like. [0081] The method for applying the curable composition of the present invention to the substrate or article is not particularly limited, and for example, roll coating, gravure coating, flow coating, curtain coating, and dipping can be used. Well-known coating methods such as coating, spray coating, spin coating, rod coating, and screen printing. After coating, the coating film is irradiated with an active energy ray to harden it. Here, as the active energy ray, any of electron rays and ultraviolet rays can be used, but ultraviolet rays are particularly preferred. As an ultraviolet source, a mercury lamp, a metal halide lamp, and an LED lamp are suitable. If the amount of ultraviolet radiation is too small, the unhardened component will remain, and if it is too large, the coating film and the substrate may be deteriorated. Therefore, it is set to 10 to 10,000 mJ / cm ² , Especially at 100 ~ 4,000mJ / cm ² The range is appropriate. In addition, in order to prevent the hardening caused by oxygen, when the ultraviolet rays are irradiated, an inert gas containing no oxygen molecules such as nitrogen, carbon dioxide, and argon is used to replace the irradiation environment, or a UV-transmissive The protective layer covers the surface of the coating film and irradiates ultraviolet rays from above. If the substrate is transparent to ultraviolet rays, a protective layer with a mold release property can be used to cover the surface of the coating film. The opposite surface is irradiated with ultraviolet rays. In addition, in order to effectively level the coating film or polymerize the acryl fluorene group in the coating film, the coating film and the substrate may be heated by an arbitrary method such as infrared rays or a hot air drying furnace before and during ultraviolet irradiation. [0082] In the hardened material layer of the hardenable composition of the present invention obtained as described above, 2 μL of droplets of ion-exchanged water were brought into contact with the liquid for 1 second, and the angle between the liquid surface and the solid surface was measured. The static water contact angle is 100 ° or more, especially 105 ° or more, and the static oleic acid contact angle is 60 ° or more, especially 65 ° or more, and becomes a water- and oil-repellent surface. In order to achieve the above-mentioned contact angle, the amount of the fluorine-containing acrylic compound of the present invention is preferably an amount capable of forming a layer having an average thickness of 10 nm or more with respect to the entire surface area of the hardened layer. Further, it is preferable that an unreacted propylene fluorenyl group does not remain on the surface. Therefore, a hardened material layer that is hardened under an inert gas atmosphere such as nitrogen or carbon dioxide is preferable. [0083] The cured product of the curable composition of the present invention thus obtained can be obtained with a refractive index (nD20 ° C) measured by an Abbe refractometer of 1.4 or less. Since the refractive index is 1.4 or less, a layer having a lower refractive index than that of glass can be formed, and the effect as an antireflection film formed on glass can be expected. The cured product of the composition composed of only the fluorine-containing acrylic compound of the present invention and the photopolymerization initiator can also be obtained under 1.4, but due to various characteristics such as film strength, abrasion resistance, transparency, etc., it is improved and refracted. In order to improve the properties such as rate adjustment, various low-refractive index inorganic fine particles such as reactive and non-reactive hollow silica fine particles, and various acrylic compounds can be blended. [0084] As described above, the curable composition containing the fluorinated acrylic compound of the present invention can harden the surface of an article through active energy rays such as ultraviolet rays, so that water-repellent and oil-repellent properties can be formed. A hardening composition of a hardening resin layer which is excellent in stain resistance, smoothness, and abrasion resistance. [0085] Furthermore, in the present invention, there is provided an article obtained by applying and curing the surface of the curable composition of the present invention on the surface. As described above, when the curable composition of the present invention is used, a cured film (cured resin layer) having excellent surface characteristics can be formed on the surface of a substrate (article). In particular, it is useful to impart water repellency, oil repellency, and stain resistance to an acrylic hard-coated surface. As a result, dirt such as fingerprints, sebum, sweat, human body fat, cosmetics, and the like, mechanical oil, and the like become difficult to adhere, and the substrate can be provided with a hard coating surface that is excellent in wiping properties. Therefore, the hardenable composition of the present invention may be contaminated by substrates (articles) which are likely to be contaminated by human fat, cosmetics, etc. due to human touch, and may be contaminated by human body fat, mechanical oil, etc. of workers Anti-fouling coating film or protective film is provided on the surface of engineering materials films and other materials used in the interior of flexible machines. [0086] The hardened film (hardened resin layer) formed using the hardenable composition of the present invention is suitable as a mobile (communication) terminal or digital media player such as a tablet computer, a notebook PC, a mobile phone, or a smartphone. Devices, electronic book readers, and other devices that are carried by human hands, watch-type and glasses-type wearable computers; liquid crystal displays, plasma displays, organic EL displays, and rear-projection displays , Various flat-panel displays such as fluorescent display tubes (VFD), field emission projection displays, CRTs, toner-based displays, TV screens, etc., display operation equipment surfaces and various optical films used in the interior, Exterior surfaces of automobiles, glossy surfaces of pianos or furniture, construction stone surfaces such as marble, decorative building materials for water facilities such as toilets, bathrooms, sinks, etc., protective glass for art exhibitions, cover windows, display cabinets, photo frames , Watch, car window glass, window glass of trains, airplanes, etc., transparent glass or transparent plastic (such as acrylic, poly Carbonate, etc.), coating films and surface protection films for various mirror members. [0087] In particular, various devices having a display input device for performing operations on a screen using a human finger or a palm, such as a touch display, such as a tablet computer, a notebook PC, a mobile phone, a mobile (communication) terminal, Digital media players, e-book readers, digital photo frames, game consoles, digital cameras, digital photography cameras, navigation devices for automobiles, automatic cash withdrawal and deposit devices, cash teller machines, vending machines, digital signage (electronic Kanban), security system terminals, POS terminals, various controllers such as remote controllers, display input devices such as panel switches for in-vehicle devices, and other surface protective films. [0088] Furthermore, the hardened film formed by the hardenable composition of the present invention is also suitable as an optical recording medium such as a magneto-optical magnetic disk, a magneto-optical disk; spectacle lenses, lenses, lenses, protective films, polarizing plates, Optical filter, lenticular lens, Fresnel lens, anti-reflection film, optical fiber and optical coupler, etc. [0089] As described above, the fluorinated acrylic compound of the present invention and the curable composition containing the same are essentially arranged in the intended article by arranging the perfluoropolyether structure of the fluorinated acrylic compound of the present invention. On the surface, excellent properties such as water repellency, oil repellency, smoothness, stain resistance, fingerprint wiping, cloth abrasion resistance, steel wool resistance, low refractive index characteristics, solvent resistance, and chemical resistance are imparted. [0090] When such a fluorine-containing acrylic compound of the present invention and a curable composition containing the same are used, as long as a well-known technology corresponding to each application is used as a basis in accordance with the combination of the formulation, the composition ratio, and the characteristics that are valued. Just choose the proper method. [0091] For example, when preparing the curable composition of the present invention, in addition to the fluorine-containing acrylic compound of the present invention, when combining various formulations in the curable composition of the present invention, if low-refractive index characteristics or In the case of using the low reflection property of this, a reactive hollow silica or a hollow silica without a reactive group or a polyfunctional acrylic compound is used, and if the film strength or abrasion resistance is improved, A polyfunctional acrylic compound is formulated in an appropriate amount, or in order to achieve a balance between hardness and flexibility, a combination of a polyfunctional acrylic compound having 6 or more functions and a acrylic compound having a trifunctional or less function can be obtained from a well-known acrylic curable composition. Insights on deployment come easily analogy. [0092] When an article is obtained by applying the curable composition of the present invention, for example, when coating a thin film substrate, it is adjusted to an appropriate coating film thickness in order to prevent interference fringes. Adjust the thickness of the film substrate to easily suppress curling, or adjust the elasticity of the substrate film to suppress the deformation of the coating film of the curable composition after curing, or the cracking of the coating film. Based on a combination of existing conditions, a screening operation is performed to select and can be easily achieved. [Examples] [0093] Hereinafter, the present invention will be specifically described by showing synthesis examples, examples, and comparative examples, but the present invention is not limited to the following examples. [Synthesis Example 1] A 200 mL four-necked flask equipped with a reflux device and a stirring device was fed with the following formula 50 g of compound (I) (Si-H group 0.034 mol), CH ₂ = CHSi (OCH ₃ ) ₃ 5.2 g [0.035 mol] and 50.0 g of hexafluorom-xylene were heated to 90 ° C. in a nitrogen environment. Here, 0.442 g of a toluene solution of platinum / 1,3-divinyl-tetramethyldisilazane complex (containing 1.1 × 10 as a Pt element) was added. ^-6 mol), keep the internal temperature above 90 ° C for 4 hours and use ¹ It was confirmed by H-NMR and IR that the peak derived from the Si-H group disappeared. Next, the hexafluorom-xylene and unreacted CH were removed by distillation under reduced pressure at 100 ° C / 267Pa for 2 hours using an evaporator. ₂ = CHSi (OCH ₃ ) ₃ Thus, 53.1 g of a compound (II) represented by the following formula was obtained as a translucent white highly viscous liquid. Compound (II) ¹ The H-NMR chemical shift is shown in Table 1. (Ph-based phenylene) [0096] [Synthesis Example 2] In a dry air environment, a 200 mL four-necked flask equipped with a reflux device and a stirring device was mixed with the following formula 50.0 g of the compound (III) (Si-H group 0.067 mol), CH ₂ = CHSi (OCH ₃ ) ₃ 10.3 g (0.070 mol), 50.0 g of hexafluorom-xylene, 0.0884 g of a toluene solution of chloroplatinic acid / vinylsiloxane complex (contains 2.2 × 10 as a Pt element) ^-7 mol), and stirred at 100 ° C for 4 hours. use ¹ After H-NMR and IR confirmed that the Si-H group disappeared, the reaction solution was cooled to room temperature. Next, the hexafluorom-xylene and unreacted CH were removed by distillation under reduced pressure at 100 ° C / 267Pa for 2 hours using an evaporator. ₂ = CHSi (OCH ₃ ) ₃ Thus, 59.2 g of a compound (IV) represented by the following formula was obtained as a translucent white highly viscous liquid. Compound (IV) ¹ The H-NMR chemical shift is shown in Table 2. [Example 1] A 100 mL three-necked flask equipped with a reflux device and a stirring device was fed with 20 g (-Si (OCH) of compound (II) obtained in Synthesis Example 1. ₃ ) ₃ 0.012mol), the following formula CH ₂ = CHCOOCH ₂ Si (CH ₃ ) ₂ 2.5 g (0.014 mol) of the compound (V) represented by OH and 40 g of methyl ethyl ketone were stirred at 40 ° C. under a nitrogen atmosphere. Here, 0.2 g of a 10% by mass methyl ethyl ketone solution of titanium tetra-2-ethylhexanolate was added, stirring was continued, and the mixture was used after 12 hours. ¹ H-NMR confirmed -Si-OCH equivalent to compound (II) ₃ The 3.5 ppm peak of the methyl group disappeared. The cooled reaction liquid was returned to room temperature (same as below 25 ° C), put into 500 mL of hexane, stirred for 1 hour, and allowed to stand for 24 hours. The obtained precipitate was dissolved with 50 g of acetone, and was evaporated with an evaporator to Distilled off at 50 ° C / 267Pa for 1 hour to obtain 19.2 g of a white ointment-like substance (A-1) represented by the following formula (VI). The compound (A-1) ¹ The H-NMR chemical shift is shown in Table 3. (Ph-based phenyl group) [0100] [Example 2] A 100 mL three-necked flask equipped with a reflux device and a stirring device was fed with 20 g (-Si (OCH) of compound (IV) obtained in Synthesis Example 2. ₃ ) ₃ 0.022 mol), 3.8 g (0.022 mol) of the compound (V), and 40 g of methyl ethyl ketone, and stirred at 40 ° C. under a nitrogen environment. Here, 0.1 g of a 10% by mass methyl ethyl ketone solution of titanium tetra-2-ethylhexanolate was added, stirring was continued, and the mixture was used after 12 hours. ¹ H-NMR confirmed -Si-OCH equivalent to compound (IV) ₃ The 3.5 ppm peak of the methyl group disappeared. The cooled reaction solution was returned to room temperature, put into 500 mL of hexane, and the obtained precipitate was dried to obtain a white ointment-like substance (A-2) represented by the following formula (VII) 20.1 g. The compound (A-2) ¹ The H-NMR chemical shift is shown in Table 4. [Examples 3 to 14 and Comparative Examples 1 to 5] [Production of hardening composition] The compounds (A-1) and (A-2) of Examples 1 and 2 and the following acrylate compounds were used And polymerization initiators to prepare the active energy ray-curable compositions of Tables 5 and 6. Acrylate compounds: (B-1) Daicel-allnex (shares) 4-functional acrylate EBECRYL 40 (B-2) pentaerythritol triacrylate (B-3) dipentaerythritol hexaacrylate (B-4) Shin Nakamura Chemical Industry 6-functional urethane acrylate U-6LPA made from (stock) Polymerization initiator: (C-1) 1-hydroxycyclohexylphenyl ketone [IRGACURE 184 made by BASF Japan (stock)] (C-2) 2 -Hydroxy-1-fluorene 4- [4- (2-hydroxy-2-methylpropanyl) benzyl] phenylphosphonium-2-methylpropane-1-one [IRGACURE 127, manufactured by BASF Japan Corporation] [0103] [0104] [0105] Preparation of Coating and Hardened Material Each composition (E1 to E12, F1 to F5) of Tables 5 and 6 was applied to a polycarbonate substrate by spin coating. After leveling at 80 ° C for one minute after coating, a conveyor-type metal halide UV irradiation device (manufactured by Panasonic Electric Industries, Ltd.) was used to irradiate the coated surface with a cumulative irradiation dose of 400 mJ / cm in a nitrogen environment. ² The composition was hardened by ultraviolet rays to obtain cured films of Examples 3 to 14 and Comparative Examples 1 to 5. [Measurement of Water Contact Angle] A contact angle meter (DropMaster, manufactured by Kyowa Interface Science Co., Ltd.) was used to measure a contact angle after dropping 2 μL of a droplet onto a cured film for 1 second. The average value of N = 5 was used as the measured value. The results are shown in Tables 7 and 8. [Measurement of Contact Angle of Oleic Acid] A contact angle meter (DropMaster, manufactured by Kyowa Interface Science Co., Ltd.) was used to measure a contact angle after dropping 5 μL of a droplet onto a cured film. The average value of N = 5 was used as the measured value. The results are shown in Tables 7 and 8. [Evaluation of Oil-Resistant Ink Resistance] An oil-based ink pen (Magic INK manufactured by Terase Chemical Industry Co., Ltd.) was used to draw a straight line on the surface of the cured film, and the ink shrinkage (cissing) was set to 0. Is ×. The results are shown in Tables 7 and 8. [Measurement of Coefficient of Dynamic Friction] In Examples 3 to 8 and Comparative Examples 1 to 4, a surface property testing machine 14FW (manufactured by Shinto Science Co., Ltd.) was used to measure BEMCOTM-3II (Asahi Kasei ( Coefficient of dynamic friction of the cured film made by))). The results are shown in Table 7. Contact area: 10mm × 35mm Load: 100g [0110] [0111] [Example 15] Using a slit applicator, the composition E-12 was applied to an aluminum substrate so that the thickness before the solvent volatilized became 250 μm, and this was air-conditioned at 100 ° C. for 2 minutes. Next, after drying under nitrogen flow at 25 ° C for 1 hour, a conveyor-type metal halide UV irradiation device (manufactured by Panasonic Electric Co., Ltd.) was used, and the cumulative irradiation amount was 400 mJ / cm in a nitrogen environment. ² The ultraviolet rays hardened the composition to obtain a light yellow transparent cured film having a thickness of 48 μm. The contact angle of water on the surface of the cured film was 111 °, and the contact angle of oleic acid was 70 °. The obtained cured film was peeled from the substrate, and the refractive index was measured using a thin-film measuring unit of an Abbe refractometer DR-A1 (manufactured by Atago) to be nD20 ° C. = 1.38.

Claims (12)

A fluorine-containing acrylic compound represented by the following general formula (1) or (2), (In the formula, Rf ¹ is independently a monovalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom, and Rf ^{2 is} based on a carbon number of 1 A bivalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group and an oxygen atom of ~ 6, and Z ¹ is independently a carbon atom having 1 to 20 carbon atoms and may include an oxygen atom, a nitrogen atom, and a silicon atom. A divalent hydrocarbon group may include a cyclic structure on the way, Z ² is independently a divalent hydrocarbon group having 2 to 8 carbon atoms, and Q ¹ is an (a + b) valence containing at least (a + b) silicon atoms. Q ² is independently a (b + 1) -valent linking group containing at least (b + 1) silicon atoms, and can form a cyclic structure. A is 1 to 10 integer, b is independently an integer of lines 1 to 10, c is independently 0, 1 or line 2, Z ¹ (2) is in the formula (1) [] enclosed by a formula or one of Z ¹ And b Z ² systems are all bonded to the silicon atoms in the respective Q ¹ or Q ² structures, R is independently a monovalent hydrocarbon group of 1 to 6, and X is independently CH ₂ = CR ¹ -COO- The group represented by Z ³ -SiR ² R ³ -O-, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, and R ² and R ³ are each independently 1 to 8 carbon atoms. Valence hydrocarbon group, Z ³ is a divalent hydrocarbon group having 1 to 8 carbon atoms, and may include a cyclic structure in the middle). The fluorine-containing acrylic compound according to claim 1, wherein Z ² in the general formulae (1) and (2) is -CH ₂ CH ₂ -or -CH ₂ CH ₂ CH _2- . The fluorine-containing acrylic compound according to claim 1 or 2, wherein X in the general formulae (1) and (2) is a group represented by the following formula, (In the formula, R ² and R ³ are the same as above, and R ⁴ is a hydrogen atom or a methyl group). The fluorine-containing acrylic compound according to any one of claims 1 to 3, which is represented by the following general formula (6) or (7), (In the formula, Rf ¹ , Rf ² , Z ¹ , Q ¹ , Q ² , a, and b are as described above, and R ⁴ is a hydrogen atom or a methyl group). The fluorinated acrylic compound according to any one of claims 1 to 4, wherein the perfluoropolyether group and the (meth) acrylfluorenyl group are bonded through a connection structure including the following structure, (Wherein Z ² is as described above), and each reactive terminal group [Z ² -SiR _c X _3-c ] _b (Z ² , R, X, b, c is such as The above-mentioned) each has a total of 4 or more (meth) acrylfluorenyl groups. A method for producing a fluorine-containing acrylic compound represented by the following general formula (1) or (2), characterized in that a fluorine-containing reactive silane compound represented by the following general formula (3) or (4), and The propylene fluorenyl group-containing silanol compound represented by the following general formula (5) is reacted, and the fluorine-containing reactive silane compound represented by the general formula (3) or (4) is based on the following general formula (8) or The fluoropolyether compound having a polyfunctional Si-H group represented by (9) and a hydrosilation reaction with a terminal unsaturated group-containing reactive silane compound represented by the following general formula (10) are obtained, (In the formula, Rf ¹ is independently a monovalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom, and Rf ^{2 is} based on a carbon number of 1 A bivalent perfluoropolyether group having a molecular weight of 400 to 20,000 composed of ~ 6 perfluoroalkylene and oxygen atom, Z ¹ is independently a carbon number of 1 to 20 and may include an oxygen atom, a nitrogen atom, and a silicon atom. A divalent hydrocarbon group may include a cyclic structure on the way, Q ¹ is a (a + b) valent linking group containing at least (a + b) silicon atoms, and may form a cyclic structure. Q ² is independently at least A (b + 1) -valent linking group containing (b + 1) silicon atoms and forming a ring structure. A is an integer of 1 to 10, and b is an integer of 1 to 10 independently. A) Z ¹ enclosed by [] or Z ¹ and b H in formula (9) are all bonded to silicon atoms in the respective Q ¹ or Q ² structure) (Where R ⁴ is a hydrogen atom or a methyl group, Z ⁴ is a divalent hydrocarbon group having 1 to 6 carbon atoms, d is 0 or 1, R is independently a monovalent hydrocarbon group of 1 to 6, and M is independently Alkoxy or alkoxyalkyl, c is 0, 1 or 2) (In the formula, Rf ¹ , Rf ² , Z ¹ , Q ¹ , Q ² , R, M, a, b, and c are as described above. Z ² is independently a divalent hydrocarbon group having 2 to 8 carbon atoms. (A Z ¹ enclosed by [] in formula (3) or Z ¹ and b Z ² in formula (4) are all bonded to the silicon atom in the respective Q ¹ or Q ² structure) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ¹ , Rf ² , Z ¹ , Z ² , Q ¹ , Q ² , (R, a, b, c, R ¹ , R ² , R ³ , and Z ³ are the same as described above). A method for producing a fluorinated acrylic compound represented by the following general formula (1), characterized in that the fluorine-containing reactive silane compound represented by the following general formula (3) and the following general formula (5) The fluorenyl group-containing silanol compound represented by the formula is obtained by reacting. The fluorine-containing reactive silane compound represented by the general formula (3) is a fluoropolymer having a terminal unsaturated group represented by the following general formula (11). An ether compound and a reactive silane compound represented by the following general formula (13) are obtained by a hydrosilylation reaction, (In the formula, Rf ¹ perfluoro-based carbon atoms by 1 to 6 oxygen atoms and extending the molecular weight of an alkyl composed of a monovalent perfluoropolyether group 400 to 20,000, Z ⁵ having an energy-based end and Si -H group is a monovalent hydrocarbon group having 2 to 20 carbon atoms in the carbon-carbon unsaturated bond, and may include an oxygen atom, a nitrogen atom, and a silicon atom, and may include a cyclic structure in the middle) (In the formula, Q ¹ is a (a + b) valent linking group containing at least (a + b) silicon atoms, and can form a ring structure. Z ² is independently a divalent one having 2 to 8 carbon atoms. Hydrocarbyl, R is independently a monovalent hydrocarbon group of 1 to 6, M is independently an alkoxy or alkoxyalkyl group, a is an integer of 1 to 10, b is an integer of 1 to 10, and c is 0 or 1 Or 2, a H and b Z ² are all bonded to the Si atom in Q ¹ ) (In the formula, Rf ¹ , Z ² , Q ¹ , R, M, a, b, and c are the same as described above. Z ¹ is independently 2 of 2 to 20 carbon atoms which may include an oxygen atom, a nitrogen atom, and a silicon atom. Valent hydrocarbon groups may include a cyclic structure on the way, and all of the a Z ¹ and b Z ² systems enclosed by [] are bonded to the silicon atom in the Q ¹ structure) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ¹ , Z ¹ , Z ² , Q ¹ , R, a, b, c, R ¹ , R ² , R ³ , and Z ³ are the same as described above). A method for producing a fluorine-containing acrylic compound represented by the following general formula (2), characterized in that the fluorine-containing reactive silane compound represented by the following general formula (4) and the following general formula (5) The fluorenyl group-containing silanol compound represented by the formula is obtained by reacting. The fluorine-containing reactive silane compound represented by the general formula (4) is a fluoropolymer having a terminal unsaturated group represented by the following general formula (12). An ether compound and a reactive silane compound represented by the following general formula (14) are obtained by a hydrosilylation reaction, (In the formula, Rf ² is a divalent perfluoropolyether group having a molecular weight of 400 to 20,000, which is composed of a perfluoroalkylene group having 1 to 6 carbon atoms and an oxygen atom. Z ⁵ is independently a terminal having one energy. A monovalent hydrocarbon group having 2 to 20 carbon atoms in the carbon-carbon unsaturated bond that undergoes an addition reaction with the Si-H group and may include an oxygen atom, a nitrogen atom, and a silicon atom, and may include a cyclic structure in the middle) (In the formula, Q ² is a (b + 1) -valent linking group containing at least (b + 1) silicon atoms, and can form a cyclic structure. Z ² is independently a bivalent having 2 to 8 carbon atoms. Hydrocarbyl, R is independently a monovalent hydrocarbon group of 1 to 6, M is independently an alkoxy or alkoxyalkyl group, b is an integer of 1 to 10, c is 0, 1, or 2, H and b (Z ² is all bonded to Si atoms in Q ² ) (In the formula, Rf ² , Z ² , Q ² , R, M, b, and c are the same as above, and Z ¹ is independently a divalent one having 1 to 20 carbon atoms and which may include an oxygen atom, a nitrogen atom, and a silicon atom. A hydrocarbon group may include a cyclic structure on the way, and all Z ¹ and b Z ² systems are bonded to silicon atoms in the Q ² structure) (In the formula, R ¹ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ³ are each independently a monovalent hydrocarbon group having 1 to 8 carbon atoms, and Z ³ is a carbon group having 1 to 8 carbon atoms. (Divalent hydrocarbon group, may include cyclic structure in the middle) (In the formula, X is independently a group represented by CH ₂ = CR ¹ -COO-Z ³ -SiR ² R ³ -O-, Rf ² , Z ¹ , Z ² , Q ² , R, b, c, (R ¹ , R ² , R ³ , and Z ³ are the same as described above). A curable composition comprising the fluorine-containing acrylic compound according to any one of claims 1 to 5. The curable composition according to claim 9, wherein the refractive index of the cured product is 1.4 or less. An article having a hardened material layer having a hardenable composition according to claim 9 or 10 on its surface. The article according to claim 11, wherein the hardened material layer has a water-repellent and oil-repellent surface having a contact angle of water of 100 ° or more and a contact angle of oleic acid of 60 ° or more.