TW201248321A - Photopolymerizable composition, and wet-area member and functional panel using same - Google Patents

Abstract

The present invention relates to a photopolymerizable composition capable of causing drops of water deposited on the surface of an article to readily fall off, and more specifically relates to a photopolymerizable composition characterized in containing: (A) a compound represented by general formula (I) (in the formula, R2 is a hydrogen atom or methyl group, n is an integer 1-20, R1 is any organic group for introducing a (meth)acryloyl group into a side chain, and m is any number selected within a range not outside a compound weight average molecular weight range of 1000-40000); (B) a photopolymerizable oligomer and/or photopolymerizable monomer which can be polymerized with the compound represented by general formula (I); and (C) a photoinitiator.

Description

201248321 VI. Description of the Invention: [Technical Field] The present invention relates to a photopolymerizable composition and a water-repellent assembly and functional panel using the same, and more particularly to a method capable of attaching to a water-repellent assembly and a functional wall A photopolymerizable composition in which the water droplets on the surface of the board are easily dropped, and the effect is long-lasting in the use environment. [Prior Art] A functional wall panel as a building material is a configuration as a wall or floor of a building. Or the components of the wall surface of the ceiling, in conjunction with the location where it is placed, to impart various functions such as sound insulation or humidity regulation. In the case of a water-repellent component such as a bathroom, a washstand, or a kitchen, which is particularly used in a house, such a functional panel is required to have an antifouling property, water resistance, and resistance to a harsh environment. Various properties such as wetness. In particular, since the water-repellent component is exposed to moisture or moisture, scale or mildew may be present, or a detergent such as a detergent or a dye may adhere to the surface to cause fouling. On the other hand, it has been tried to impart good water repellency to the component by adding a low-energy compound having a small surface free energy and reducing the surface free energy to the surface of the member to: The low surface free energy compound is a hydrophobic material such as a fluororesin or a deuterated S. For example, Patent Document 1 discloses a water-repellent component having a surface-hardening compound having a surface-free free energy compound, and further reveals that the low-surface free-energy compound is an oxime resin compound or a fluororesin compound. Further, Patent Document 2 discloses a resin molded body in which a low surface free energy layer is formed on the surface of the base resin to make the surface of the molded body a lower surface free energy surface than the surface of the base resin, and further revealed. The contact angle of the surface of the resin molded body with water is 9 以上 or more and 170 degrees or less, and the roll angle of the surface of the resin molded body and water is 1 degree or more and 80 degrees or less. Patent Document 1: JP-A-2002-69378, JP-A-2000-233156, however, "When water is bounced on the surface of the low surface free energy produced by using the low surface free energy compound described above, A spherical water droplet is formed on the surface but it is common that the water droplet strongly adheres to the surface without falling. Then, although the surface has been roughened and the like, the attached water droplets have been dropped from the surface, but the surface after roughening or the like has a problem of durability and easy adhesion of the dirt. Thus, the present invention has been made in view of the above problems, and an object thereof is to provide a photopolymerizable composition which is capable of allowing water droplets adhering to the surface of an article to fall easily and having a long-lasting effect in the use environment. Further, another object of the present invention is to provide a water-repellent unit and a functional wall panel having a coating layer formed by curing the photopolymerizable composition and having good water slidability. 4 201248321 SUMMARY OF THE INVENTION The inventors of the present invention have conducted further studies in order to achieve the above object, and as a result, it has been found that by using a ruthenium-containing compound having a specific structure as a constituent component of the photopolymerizable composition, water droplets capable of adhering to the surface of the article can be obtained. The present invention is completed by a photopolymerizable composition which is easy to fall and which has a long-lasting effect in the use environment. That is, the photopolymerizable composition of the present invention comprises: (A) a compound represented by the following chemical structural formula (I): OHg^Si

Sid ch3 ch3 Si-( I R1 R2 -SiCH3^

(I O-C-C = CHj

II

Wherein R 2 is a hydrogen atom or a fluorenyl group, n is an integer of 1 to 20, R 1 is an arbitrary organic group for introducing a (meth) acryl fluorenyl group into a side chain, and m is selected from a weight average molecular weight of the compound. Any number in the range of 1000 to 40000; (B) a photopolymerizable oligomer and/or a photopolymerizable monomer capable of being polymerized with the compound represented by the above chemical formula (I); and (C) a photopolymerization initiator. The photopolymerizable composition of the present invention preferably further comprises (D) a fluorine-containing compound. Here, the mass ratio (A/D) of the compound represented by the above formula (A) to the (D) gas-containing compound is preferably in the range of 201248321 0.2 to 10.0, more preferably 0.4 to 5.0. range. In a preferred embodiment of the photopolymerizable composition of the present invention, the content of the compound represented by the chemical structural formula (1) when the (B) light $(A) oligomer and the photopolymerizable monomer are 100% by mass in total $0.01 to 5% by mass, and/or the content of the (D) fluorochemical compound ▲' is a photopolymerizable oligomer and a photopolymerizable early body totaling 1 QQ L () υ 〇 〇 〇 / /, It is 0 to 5 mass%. When the content ratio represented by the chemical structural formula (I) is less than 0.01% by mass, the ability to sufficiently exert the energy of the σ surface is not sufficient. If it is more than 5% by mass, the photopolymerizable low surface or photopolymerization is used. The compatibility of the monomer is deteriorated and the addition effect & aggregates to saturation. On the other hand, the raw material of the photopolymerizable composition costs. In another preferred embodiment of the photopolymerizable composition of the present invention, the "polymerizable oligomer" is a (meth) methacrylate oligomer having a 1,2-polybutylene oxide unit. In another preferred embodiment of the photopolymerizable composition of the present invention, the polymerizable monomer has a solubility parameter (SP value #2G () Cf/em3). Here, the photopolymerizable monomer is fine. (Expression (II): (CH2=CR3C00) pr4, R3 is a hydrogen shoulder or a methyl group, R4 is a p-valent hydrocarbon group having 5 to 20 carbon atoms, and P is an integer of 1 to 4. Further, the present invention The water-repellent component has a coating layer formed by curing the photopolymerizable composition, and a base material layer. The functional wall panel of the present invention has a composition in which the photopolymerizable 6 201248321 composition is cured. a coating layer, and a substrate layer. According to the present invention, there is provided a compound comprising (A) the compound represented by the above chemical structural formula (I), and (B) polymerizable with the compound represented by the chemical structural formula (I). The photopolymerizable oligomer and/or the photopolymerizable monomer and the (C) photopolymerization initiator can easily drip water droplets adhering to the surface of the article. Further, it is possible to provide a water-repellent composition which is long-lasting in the use environment, and a water-repellent assembly and a functional wall having a coating layer formed by curing the photopolymerization = product and having good water slidability. (Embodiment) The photopolymerizable composition of the present invention is characterized by containing (A) the compound represented by the above chemical structural formula (1) and (B). The photopolymerizable oligomer and/or photopolymerizable monomer which is polymerized with the compound represented by the above chemical formula (1) and (C) photopolymerization initiator may further contain other components as needed. 13 Photopolymerization of the present invention The compound represented by the above chemical formula (I) is added to the composition, and the compound is not only water repellency but also excellent in water slidability. Thus, the article coated with the photopolymerizable composition of the present invention is particularly a water-repellent component. And the functional wall panel has a high water slidability of the coating layer, so that the water droplets adhering to the surface of the coating layer can be dropped. <<(A) The compound represented by the above chemical structural formula (1)>> 7 201248321 The photopolymerizable graded product of the invention contains a compound. In the chemical structural formula (1), ', ^ or methyl, R is used for the (meth) propylene 2 = bond spacers. = : If R1 has a stretching group, the compound represented by (1) can be used as a photopolymerizable composition; and the other part can be a straight or difficult m-filled base resin. Alkenyl, vinyl, :methene a. Specifically, 'exemplified is a methyl group,' fine base, tetracaine, hexamethyl, κ methyl vinyl, 2: its base, fourteen Dilute, octadecyl, 2-methylhaylidene, d-based, 1-mercapto-seven, sulphate, sulphate, 2,3,6-triterpene, earth, 2_A _5_ethyl, 7-fluorenyltetradecyl, dilute, 6-ethyl decadecene methyl octadecyl, 8 dimethyl hexadecenyl, 7,12· Dikiladyl-7-ethylhexadecylcarbamate, κ; ^ human 曱 基, 7,10 曱 曱 _ _ 十八 十八 十八 十八 乙烯基 、 、 乙 乙 乙 乙 乙 乙 乙 乙 乙Hexadecenyl, 7,12.n octadecyl, 7-vinyl winter dimethyl-7,11_18 bis^^^ Dilute dimethylene group, and 8,11, other than Rl ^ are exemplified ⑽ group. By making the compound of the formula 201248321 a hydrophilic group, it is possible to ensure a wide compatibility with the substrate and the fat. This will add the appropriate 1 to the series. Here, the ether group is represented by -(〇R,)q_, and R' is preferably a linear or branched alkyl group having 1 to 3 carbon atoms. These may be individually bonded, or mixed and then bonded. The mixing may be in the form of a block or a random number, and the complex number q is an integer from 1 to 100. n in the compound represented by the above formula (1) is an integer of 1 to 20. By containing a (fluorenyl) acrylonitrile group in the structure, when irradiated with light, (B) a photopolymerizable oligomer which can be polymerized with the compound represented by the above chemical structural formula (1), or light The polymerization is carried out by reacting the monomer. Thereby, the function can be continued even if the wiping or the like is repeated. On the other hand, S η is more than 20, because (4) the compound represented by the above chemical structural formula (1) and (9) are photopolymerizable oligomeric and/or photopolymerizable singles capable of polymerizing with the compound represented by the above chemical formula (1). The compatibility of the body will be too good, so it will be difficult to exist ^ the most surface 'and can not fully function. Further, the range of η of 2 to 6 is the best. (Α) The weight-to-flat SI amount ρ of the compound represented by the above chemical structural formula (1) is preferably in the range of the touch to the side. The weight average molecular weight can be made into a calibration curve as standard, and it can be consulted from the test. A GTC mobile layer solvent can be a tetrahydrogen detector or the like. If the above-mentioned underSt is used, the above-mentioned average molecular weight is less than the above, and the relative amount of the dimethyl 9 201248321-based oxane moiety in the compound represented by the formula (1) is lowered, so that in order to exert sufficient scoop j will have to increase the amount added. On the other hand, if the weight average molecular weight is greater than 4_〇' μ and (B) is compatible with the above-mentioned chemical structural formula (1), the compatibility of the photopolymerizable oligomer and/or photopolymerizable monomer which is not polymerized by the compound It will be significantly reduced and lead to separation. From this point of view, m is an optional number selected from the group consisting of the compound of the formula (I) having a weight average molecular weight in the range of from 1,000 to 40,000. In the photopolymerizable composition of the present invention, when the content of the compound represented by the above chemical formula (1) is (1) when the photopolymerizable oligomer and the photopolymerizable monomer are in a total amount of 1% by mass, It is preferably in the range of 〇〇1 to 5 mass%, more preferably in the range of 〇1 to 3 〇 mass%. Here, the content of the compound represented by the chemical structural formula (1) is the amount of the active ingredient of the compound represented by the chemical structural formula (1) (the amount of the solid portion), and the content of the compound represented by the structural formula (I) is 〇% by mass. As described above, the water repellency and the water slidability of the article coated with the photopolymerizable composition of the present invention can be sufficiently improved, and it is 5 mass. /. In the following, compatibility with the (B) photopolymerizable oligomer and/or monomer is good, and a uniform cured product can be obtained. «(B) Photopolymerizable oligomer and/or photopolymerizable monomer The (B) photopolymerizable oligomer and/or photopolymerizable single system used in the photopolymerizable composition of the present invention can The polymerizable unsaturated vinyl compound obtained by polymerizing the compound represented by the above chemical formula (I) (for example, having one or more radically polymerizable (fluorenyl) acrylonitrile groups [CH2=CHCO- or CH2=C(CH3) CO-] compound), unsaturated 201248321 and polyester resin, polybutadiene resin, and the like. In the present invention, the photopolymerizable oligomer and/or the photopolymerizable single system of the component (B) are other than the compound represented by the above chemical formula (1). Further, the mass ratio of the (B1) photopolymerizable oligomer to the (B2) photopolymerizable monomer is 100:0 to 0:丨〇〇, preferably 80:20 to 20:80, more preferably 30: 70~70: 30 range. When the amount of the photopolymerizable monomer to be added is too small, the viscosity of the obtained photopolymerizable composition increases, and the coating property is deteriorated, and physical properties such as chemical resistance and chemical dyeability cannot be sufficiently ensured. The possibility of characteristics. When the amount of the photopolymerizable monomer added is too large, the flexibility of the coating film is lowered and the friability tends to be high. «<(Β1) Photopolymerizable oligomer>> The photopolymerizable oligomer preferably has more than one propylene fluorenyloxy group [CHpCHCOO-] or a decyl propylene methoxy group [CH2=C ( The (meth) acrylate oligomer of CH3)COO-] is particularly preferably a (fluorenyl) acrylate oligomer having a 1,2-polybutylene oxide unit. Since the (mercapto) acrylate oligomer having a 1,2-polybutylene oxide unit has a low polarity, it has good compatibility with the compound of the chemical structural formula (1), and a chemical structure can be widely added. (1) Compound. Therefore, even when the amount of the compound of the chemical structural formula (I) is large, the white turbidity, the layer separation, and the like can be suppressed, so that the appearance after hardening can be improved, and the water-repellent component and the functionality thereof can be used. The siding forms a good appearance. Moreover, since the resin obtained by hardening the photopolymerizable composition has high hydrophobicity, it is highly resistant to stains such as detergents or hair dyes used in water and water places 201248321, and dirt is difficult to be used. Adhesion and long-term stability of water skating will be better. The above (meth) acrylate oligomer is specifically exemplified by an amine ester (mercapto) acrylate oligomer, an epoxy (mercapto) acrylate oligomer, and an ether (meth) acrylate. A (mercapto) acrylate oligomer such as a polymer, an ester (meth) acrylate oligomer, a polycarbonate (mercapto) acrylate oligomer, or a fluorene (meth) acrylate. These (fluorenyl) acrylate oligomers can be synthesized in the following manner: polyethylene glycol, polyoxypropylene glycol, polytetramethylene ether glycol, bisphenol A epoxy resin, phenol novolak epoxy resin And an adduct of a polyhydric alcohol and ε-caprolactone, and the (mercapto)acrylic acid; or an amine esterification of a polyisocyanate compound and a (fluorenyl) acrylate compound having a hydroxyl group. The photopolymerizable oligomer may be any of a monofunctional oligomer, a difunctional oligomer, and a polyfunctional oligomer, from the viewpoint of achieving an appropriate crosslinking density of the obtained photopolymerizable composition. Preferably, it is a polyfunctional oligomer. Among these photopolymerizable oligomers, an amine ester (meth) acrylate oligomer excellent in chemical resistance is used from the viewpoint of imparting good characteristics as a water-repellent module and a functional wall. good. The amine ester (mercapto) acrylate oligomer can be synthesized from the amine phthalate prepolymer by, for example, a polyhydric alcohol and a polyisocyanate, and then a (hydroxy) acrylate having a hydroxyl group is added to the amine hydrazine. Manufactured from an acid ester prepolymer. The polyol system 12 201248321 used for the synthesis of the above amine phthalate prepolymer has a compound of a plurality of hydroxyl groups (-OH), and specific examples thereof include a polyether polyol, a polyester polyol, and a polytetradecene glycol. Polybutadiene polyol, alkylene oxide modified polybutadiene polyol, and polyisoprene polyol. These polyols may be used singly or in combination of two or more. In addition, the above poly-polyol can be obtained by polyaddition, for example, ethylene glycol, propylene glycol, glycerin, trihydroxydecyl propane, pentaerythritol, sorbitol, etc., addition of ethylene oxide or propylene oxide Equivalent alkylene oxide. Further, a polyether polyol can also be obtained by ring-opening polymerization. Examples of such a polyether polyol include polytetradecene glycol obtained by ring-opening polymerization of tetrahydrofuran (THF). The above polyester polyol can also be obtained by addition polymerization, for example, ethylene glycol, diethylene glycol, 1,4-butanediol, 1,6-hexanediol, propylene glycol, trihydroxydecylethane, A polyhydric alcohol such as trihydroxydecylpropane is obtained with a polybasic acid such as adipic acid, glutaric acid, succinic acid, sebacic acid, pimelic acid or suberic acid. Further, a polyester polyol can be obtained by ring-opening polymerization, and such a polyester polyol is exemplified by a lactone-based polyester polyol obtained by ring-opening polymerization of ε-caprolactone. The above polyol can be produced by using a butylene oxide modified polyol to produce a (meth) acrylate oligomer having the above 1,2-polybutylene oxide unit. The butylene oxide-modified polyol is a polyether polyol obtained by adding 1,2-butylene oxide to a polyol in the presence of a basic catalyst. Further, a polyether polyol obtained by adding polyoxyalkylene such as propylene oxide to a poly(1,2-butylene oxide) may be added. In this case, the ratio of cerium to other alkylene oxide is 20:80 to 100:0, preferably 50:50 to 100: 〇 in a molar ratio of 13 201248321. The GPC-based weight average molecular weight of these butylene oxide modified polyols is usually from 100 to 15,000, preferably from 5 to 5 Å. The above polyisocyanate is a compound having a complex isocyanate group (-NCO), and specific examples thereof include indane diisocyanate (TDI), diphenyldecane diisocyanate (MDI), and crude diphenylnonane diisocyanate (Crude MDI). ), isophorone diisocyanate (IPDI), hydrogenated diphenylnonane diisocyanate, hydrogenated phthalic acid diisocyanate, hexadecyl diisocyanate (HDI); or such isomeric cyanuric acid modified product, carbon Diterpenoid imine modification, glycol modification, and the like. These polyisocyanates may be used alone or in combination of two or more. It is preferred to use a catalyst for the esterification reaction in the synthesis of the above urethane prepolymer. Examples of the catalyst for the esterification reaction include dibutyltin dilaurate, dibutyltin diacetate, dibutyltin thiocarboxylate, dibutyltin dimaleate, dioctyltin thioglycolate, tin octoate, and monobutyltin. An organic tin compound such as an oxide; an inorganic tin compound such as vaporized stannous oxide; an organic ship compound such as octanoic acid; a cyclic amine such as triethylenediamine; and an organic sulfonate such as p-toluenesulfonic acid, methanesulfonic acid or fluorosulfuric acid. Acid; sulfuric acid, acid, high-acid acid and other inorganic acids; sodium alkoxide, argon oxidation clock, aluminum acoluminate, sodium hydroxide, etc.; tetrabutyl silicate, tetraethyl titanate, tetrabasic acid A titanium compound such as propyl ester; a silk compound, a quaternary ammonium salt or the like. Among the catalysts, organotin compounds are preferred. These catalysts may be used singly or in combination of two or more. The amount of the above-mentioned polyol used in the above-mentioned polyol is preferably in the range of 0.001 to 2 % by mass based on 1% by mass of the above polyol. Further, the (fluorenyl) acrylate having a hydroxyl group added to the urethane prepolymer has one or more hydroxyl groups and has one or more (meth) acryloyl groups [CH2=CHC〇〇_ or Compound of CH2=C(CH3)COO-]. The (meth) acrylate having a hydroxyl group may be added to the isocyanate group of the above polyurethane prepolymer. The hydroxy group-containing acrylate is exemplified by 2-hydroxyethyl (decyl) acrylate, 2-hydroxypropyl (decyl) acrylate, pentaerythritol tri(decyl) acrylate, and the like. These (meth) acrylates having a hydroxyl group may be used singly or in combination of two or more. By adding the photopolymerizable oligomer, the glass transition temperature of the coating layer obtained by curing the photopolymerizable composition can be optimized, and excellent water repellency and water slidability can be obtained. Photopolymerizable composition. <«(B2) Photopolymerizable monomer>>> The photopolymerizable monomer is preferably one or more acryloxy groups [CHpCHCOO-] or decyl propylene oxy group [CH2=C(CH3)) The (meth) acrylate monomer of COO-] may be any one of a monofunctional monomer, a bifunctional monomer, and a polyfunctional monomer. Monofunctional monomers are exemplified by isodecyl (meth) acrylate, decyl (meth) acrylate, tricyclononyl (meth) acrylate, dicyclopentanyl (meth) acrylate, (fluorenyl) Dicyclopentenyl acrylate, cyclohexyl (meth) acrylate; benzyl (meth) acrylate, 4-butylcyclohexyl (meth) acrylate, 15 201248321 (fluorenyl) propylene morpholine, (曱2-hydroxyethyl acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, decyl (meth) acrylate, ethyl (meth) acrylate, (methyl) ) propyl acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl acetonate, tert-butyl acrylate (meth) acrylate, pentyl vinegar (methyl) acrylate (methyl) isoamyl acrylate, hexyl (meth) acrylate, heptyl (mercapto) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethyl (meth) acrylate Hexyl hexyl ester, (decyl) decyl acrylate, decyl methacrylate, isodecyl (meth) acrylate, (曱) undecyl acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, octadecyl methacrylate, (carbyl) methacrylate Palmityl (meth)acrylate, isostearyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, butoxyethyl (meth)acrylate, ethoxylated (meth)acrylate Ethylene glycol ester, polyoxyethylene nonylphenyl ether acrylate, phenoxyethyl (meth) acrylate, polyethylene glycol mono(decyl) acrylate, polypropylene glycol mono(decyl) acrylate , (mercapto) methoxyethylene glycol acrylate, ethoxyethyl (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, decyl propylene glycol acrylate (Mercapto) dimethylaminoethyl acrylate, diethylaminoethyl (meth) acrylate, 7-amino-3,7-didecyl octyl (decyl) acrylate, and the like. Examples of the bifunctional monomer are ethylene glycol di(indenyl)acrylate, tetraethylene glycol di(mercapto)acrylate, triethylene glycol vinegar di(meth)acrylate, and bis(indenyl)acrylic acid-1. , 4-butanediol vinegar, 16-1,4-hexadediolate di(meth)acrylate, di(meth)acrylic acid, diol glycol ester, neopentyl glycol di(meth)acrylate Tris(2-hydroxyethyl)isocyanurate group II

201248321 Two di(meth) acrylates of decyl bisulphate bismuth bismuth phthalate, bisphenol A alkylene oxide addition diol, hydrogenated bisphenol A alkylene oxide addition binary An epoxy (meth) acrylate obtained by adding a (meth) acrylate of an alcohol or a (meth) acrylate to a diglycidyl ether of bisphenol A. Examples of polyfunctional monomers are trihydroxymercaptopropane tris(mercapto) acrylate, ethoxylated trishydroxypropyl propane tri(meth) acrylate, propoxylated trimethylolpropane tris(fluorenyl). Acrylate, pentaerythritol tri(indenyl) acrylate, pentaerythritol tetrakis(meth) acrylate, dipentaerythritol hexakisyl acrylate, bis(trihydroxydecylpropane)tetrakis(meth) acrylate, dipentaerythritol Hydroxypenta(indenyl) acrylate and the like. These (fluorenyl) acrylate monomers may be used singly or in combination of two or more. The photopolymerizable monomer is preferably a photopolymerizable monomer having a solubility parameter (SP value eO.OQ/cm3) of 0.5 or less. Here, the sp value (8) is generally defined by the Mohr evaporating energy of the liquid and the Moir volume (V) ': the SP value (δ) = (ΔΕν / ν) 0·5. Furthermore, according to the Fedors method, the SP value can be estimated only from the chemical structure (refer to "Solubility Parameter Values", Polymer Handbook (卩〇1丫11161-11&11北〇〇1<;), The fourth edition ( ).3 to 11 (11: 叩 et al 17 201248321 In addition, in this (4) book, the SP value is purely based on the value of Fed 〇 rs = 'this value listens to the photopolymerizable monomer (B) polarity The SP value of the photopolymerizable monomer is preferably 丨9 6 (J/cm3) 〇·5 or less, and more preferably 19.4 (JW or less. Further, although the lower limit of the value is not particularly limited, In general, the photopolymerizable monomer is preferably a compound represented by the following formula (11): (CH2=CR3COO)pR4. In the formula (II), R3 is a hydrogen atom or a methyl group, and R4 is a P-valent hydrocarbon group having 5 to 20 carbon atoms, but does not contain a hetero atom, and may be a chain or a ring. Further, -CH2· in the group may also be used. _CH=CH-substitution. p is an integer of i to 4. That is, in the above formula (II), for example, in the case of a chain-like saturated monomer, 'n=l, R4 is an alkane having 5 to 20 carbon atoms. Base, when n=2, R4 is an alkylene group having a carbon number of 5 to 20. Further, if it is a chain In the case of a monomer, when n=3, R4 is a three-substituted alkane triyl having a carbon number of 5 to 20, and when n=4, R4 is a aikane tetrayl having a carbon number of 5 to 20. The above R4 is, for example, an alkyl group such as _CH2CH3, -CH2CH2CH3, -CH(CH3)CH3, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl or cyclodecyl, -CH2CH2-, -CH2CH2CH2-, -CH ( CH3) CH24#, a trisubstituted alkyl group represented by CH3CH2C(CH2-)3, or a tetrasubstituted alkyl group represented by C(CH2-)4, etc. When the carbon number of R4 is less than 5, it is a chain In the case of a hydrocarbon group, the SP value of the monomer tends to increase. 'In the case of a cyclic hydrocarbon group, it is difficult to obtain itself. When the carbon number of R4 exceeds 20, the hydrocarbon group of the ring 18 201248321 is formed. In this case, the crosslinking density of the obtained photopolymerizable composition tends to decrease. When the crosslinking density is excessively lower than necessary, the coloring agent such as a hair dye easily penetrates into the interior of the coating layer, so the wall plate It is possible to be dyed. Specifically, the monomer represented by the above formula (η) is exemplified by isodecyl (meth)acrylate or hexanediol di(meth)acrylate. , dimethyl tricyclic oxime di(methyl) acrylate, (mercapto) propionate isoamyl, (meth) acrylate lauryl, (meth) acrylate triterpene, ( Isomyristyl methyl methacrylate, octadecyl acrylate (mercapto) acrylate, 3-methyl-1,5-pentanediol bis(indenyl) acrylate, bis(indenyl)acrylic acid neodymium: alcohol Ester, cyclohexanedimethanol di(meth)acrylate, bis(indenyl)acrylic acid 1,9-nonanediol ester, trishydroxypropylpropane tris(meth)acrylate, pentaerythritol tetra ( Methyl) acrylate. Wherein 'preferably bis(indenyl)acrylic acid 1,9-nonanediol ester, bis(indenyl)acrylic acid 1,6-hexanediol, isodecyl (meth)acrylate, dihydroxyindole Tricyclodecane bis(indenyl)propanoate, more preferably 1,9-nonanediol di(indenyl)acrylate, di-methylbicycloindole bis(methyl) acrylate. If such a monomer has a more suitable SP value, it will show a good tendency to low polarity, which not only improves the antifouling property of the obtained water-repellent component and functional wallboard, but also further improves chemical resistance. Drug resistance, dye resistance. The photopolymerizable monomer having a solubility parameter (SP value) of 2 〇.〇(J/cm3y)_5 or less, particularly a monomer represented by the formula (II), has a low polarity, and thus has a chemical structural formula. The compound of (1) has good compatibility, and a compound of the formula (I) can be added in a wide range. Therefore, even when the amount of the compound of the chemical formula (i) of 19 201248321 is large, white turbidity, layer separation, and the like can be suppressed, so that the appearance after hardening can be improved, and the water-repellent component using the same can be used. Functional siding forms a good appearance. Further, since the resin obtained by curing the photopolymerizable composition has high hydrophobicity, the dye is highly resistant to stains such as a stripping agent or a hair dye used in water and water, and the dirt is difficult to be used. The long-term stability of the adhesion 'slip water' will be better. Further, the number of functional groups of the photopolymerizable monomer is usually 丨6, preferably 1-4. Further, when the number of functional groups is 1, the crosslinking density tends to increase, but when the number of functional groups is 2 to 6, preferably 2 to 4, crosslinking with a photopolymerizable composition can be appropriately maintained. In the opposite direction, it can be inferred that it is particularly easy to effectively inhibit the penetration of the dye. If (4), the water-repellent assembly and the functional wall panel are dyed, in which case not only good antifouling properties can be obtained, but also a coating layer having a suitable hardenability can be obtained while maintaining chemical resistance and dyeing resistance. The water-repellent component and the power J element I combined with the hairpin agent ー 发 ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光 光The action of a single substance with (B) photopolymerizable oligomer and/or light = opening and closing. The photopolymerization initiates diaminoamine benzoic acid, 4•dimethylamine benzoic acid, 2,2-dimethyl benzoate, acetophenone diethyl hydrazine, alkoxy phenylethyl 20 201248321 ketone, benzyl Didecyl ketone, benzophenone and 3,3-dimercapto-4-methoxybenzophenone, 4,4-dimethoxybenzophenone, 4,4-diamine diphenyl a benzoyl derivative such as a benzophenone derivative such as ketone or a benzhydrazinium alkanoate, a bis(4-dialkylaminophenyl) ketone, a benzyl group or a benzyl fluorenyl ketone, or a benzoin And benzoin derivatives such as benzoin isobutyl ester, benzoin isopropyl ester, 2-hydroxy-2-mercaptoethyl phenyl ketone, 1-hydroxy-cyclohexyl-phenyl-hydrazine, mountain _, xanthone and α Sedoxone derivative, hydrazine, 2,4,6-trimercaptobenzylidene diphenylphosphine oxide, bis(2,6-dimethoxyphenylphenyl)-2,4,4 - tridecylpentylphosphine oxide, bis(2,4,6-trimercaptophenyl)phenylphosphine oxide, 2-methyl-1-(4-mercapto-f-phenyl) -2-morpholinylpropan-1-one, 2-benzyl-2-dimethylamine-1-(4-morpholinylphenyl)-butanone-1 and the like. These photopolymerization initiators (C) may be used singly or in combination of two or more. In the photopolymerizable composition of the present invention, the amount of the (C) photopolymerization initiator added is preferably 0.1 to 10 by mass when the (B) photopolymerizable oligomer and the photopolymerizable monomer are 100% by mass in total. The range of %. When the amount of the (C) photopolymerization initiator added is 0.1% by mass or more, the polymerization reaction can be sufficiently initiated. On the other hand, when the amount is more than 10% by mass, the effect of initiating the polymerization reaction is saturated, and the photopolymerizable composition is obtained. The cost of raw materials will increase. «(D) Fluorine-containing compound The photopolymerizable composition of the present invention preferably further contains (D) a fluorine-containing compound. By containing the (D) fluorine-containing compound, the water repellency and water slidability of the photopolymerizable composition can be further improved. 21 201248321 Any fluorine-containing compound can be used for the above fluorine-containing compound. When durability is considered, it is a photopolymerizable oligomer and/or a photopolymerizable monomer which can be polymerized with the compound of the chemical structural formula (1) containing the compound (A) of the chemical structural formula (1). In the sense that (C) the photopolymerizable composition of the photopolymerization initiator reacts and is immobilized in the system, it is preferred that the (D) fluorine-containing compound also has a photopolymerizable reactive group in the structure. Specifically, a photopolymerizable compound containing a perfluoroalkyl group like perfluorooctylethyl acrylate is exemplified. More specifically, if it is also a product name, Illustrate is LIGHT ACRYLATE FA-108 [Kyoeisha Chemical Co., Ltd.], RS-75 [DIC Co., Ltd.], OPTOOL DAC-HP [DAIKIN INDUSTRIES, LTD. 〕, MODIPER F200, F600, F3035 [Nippon Oil Co., Ltd.], HYPERTECH FA-200 [曰Product Chemical Industry Co., Ltd.], etc. These (D) fluorine-containing compounds may be used singly or in combination of two or more. The mass ratio (A/D) of the compound represented by the above formula (A) to the above-mentioned (D) fluorine-containing compound is preferably in the range of 0.2 to 10.0, more preferably in the range of 0.4 to 5.0. Here, in the mass ratio (A/D)-based photopolymerizable composition, (A) the ratio of the compound represented by the chemical structural formula (I) to the active component of the (D) fluorine-containing compound (solid portion ratio). When the mass ratio (A/D) is 0.2 or more, the effect of both the high water repellency of the (D) fluorine-containing compound and the water slidability of the compound represented by the above (A) chemical structural formula (I) can be expected. In the case of 〇4 or more, the concentration of the fluorine-containing compound on the surface and the compound represented by the above chemical structural formula (1) may be changed to 22 201248321 π ', so that the effect described above can be expected more, and if it is 10.0, it can be C. When the compatibility with the (Β) photopolymerizable oligomer and/or the photopolymerizable precursor is less than 5 (), more excellent compatibility can be obtained. In the photopolymerizable composition of the invention, the (D) fluorine-containing compound-containing cerium is preferably 〇 5 mass when the (8) photopolymerizable oligomer and the photopolymerizable monomer are in a total of 100 Å. The range of % is more preferably the range 11 of 0·1~f%. Here, the content of the compound containing (D) is (D) the amount of the active ingredient of the fluorinated compound (the amount of the solid portion). When the content of the (D) fluorine-containing compound is 5 f% by volume or less, the effect of lifting, water repellency, and water sliding can be sufficiently exerted. On the other hand, when the content is more than 5% by mass, the characteristic surface and the cost surface are obtained. It is not meaningful to look at it. If it is less than or equal to 3% of the amount of mussels, it can be expected that the water-repellent and the slippery water can be sufficiently improved in practical use. When the mass is at least the above, the effect of improving the water repellency and the water slidability of the photopolymerizable composition is greatly improved. «Others" The photopolymerizable composition of the present invention may further contain a photosensitizer as needed in consideration of the required hardening reactivity, stability, and the like. The photosensitizer absorbs light by being irradiated with light, and the energy or electrons move toward the polymerization initiator to initiate polymerization. The photosensitizer is exemplified by isoamyl P-dimercaptoamine benzoate and the like. The amount of the photosensitizer to be added is preferably in the range of 0.1 to 10% by mass, based on the total amount of the photopolymerizable oligomer (B) and the photopolymerizable monomer. Further, the photopolymerizable composition of the present invention has a curing reactivity, stability, and the like, and may contain a polymer as needed. Examples of the polymerization inhibitor are hydroquinone, hydroquinone monomethyl ether, phenylbenzene, 2,4 dimethyl-6-tert-butylphenylhydrazine, 2,6•di-tert-butylphenol, and butylhydroxyfenate. Ether, 3-hydroxy thiophenol, & nitroso-naphthylquinone: for the stupid, 2,5_two subtractive material. When the amount of the above-mentioned (Β) photopolymerizable oligomer and the photopolymerizable monomer is 100% by mass or less, it is preferably in the range of 0% to 0.001% by mass. Further, the photopolymerizable composition of the present invention may contain, as a diluent solvent, an organic solvent such as an ether 'S and an ester'. The organic solvent is exemplified by propylene glycol monomethyl ether acetate (ΡΜΑ), methyl ethyl ketone (oxime), sulfhydryl group. Isobutyl ketone (MIBIC), acetone or butyl lactate. These diluent solvents may be used alone or in combination of two or more. The photopolymerizable composition of the present invention can be applied to a surface of a substrate by using a diluent bath as described above, as needed, in the form of a coating liquid. The coating method may be a known method, and examples thereof include a gravure coating method, a co-coating method, a reverse coating method, a knife coating method, and a die coating method. Die coating, lip coating, doctor coating, extrusion coating, slide coating, wire bar coating Method, curtain coating method, extrusion coating method, spin coating method, and the like. <Water-repellent unit> 24 201248321 The water-repellent unit of the present invention is characterized in that it has a coating layer formed by curing the above-mentioned light-aggregating composition, and a base material layer. The water-repellent component of the present invention is a water-repellent component requiring surface exemplification, for example, a flow table, a washbasin, a wall material for a bathroom, a bathtub, a bathroom ceiling material, a bathroom floor panel, a bathroom, a toilet, a storage, and a storage. Water tanks, etc. <Functional Wall Panel> The functional panel of the present invention is characterized in that it has a coating layer formed by curing the photopolymerizable composition, and a substrate layer, for example, the coating layer is preferably formed on the wire. On the floor. The thickness f of the entire inclined wall panel of the present invention is preferably 2.5 mn^h. Further, the upper limit of the thickness of the entire functional panel is not particularly limited, and the coating layer may be formed on both the surface and the inner surface of the substrate layer. In addition to these base material layers and coating layers, it is also possible to form an inter-sheet layer of various materials between the layers as needed. The layer structure n is excellent in water repellency because the coating layer is as described above. And water slick, so it is desirable that the '(four) coating layer is the outermost layer of functional Wei. The middle layer raises the ruthenium, improves the adhesion of the lining layer, or enhances the style of the Wei-wei, and gives the decorative layer of the pattern and color. Since the water-repellent unit and the functional wall panel of the present invention thus obtained have the coating layer formed on the base material layer, the water-repellent water and the water-repellent property are excellent, and the hot water resistance or the dyeing resistance is excellent. It is also true that (4) scales are used for gambling on the surface, and even if the sputum containing acid or test is strong (4), it is not easy to cause deterioration or deterioration. Further, even if a dye such as a hair dye is used, discoloration and dyeing are unlikely to occur. Accordingly, the functional panel of the present invention is particularly suitable as a functional panel for a bathroom or kitchen disposed in a dwelling. «Coating J>> The coating layer can be formed on the substrate layer by applying the photopolymerizable composition to a substrate and then photocuring it. The method of hardening the light is generally a method of irradiating light such as ultraviolet rays. The surface on the substrate layer for forming the coating layer may be only one of the surface or the back surface, or may be double-sided, and may be appropriately selected as needed. Further, when the amount of light irradiation when the photopolymerizable composition is cured is ultraviolet rays, the irradiation intensity is usually 2 〇 2 2 〇〇〇 mW/cm 2 and the irradiation amount is 100 5,000 to 5000 m J/cm 2 . The polymerizable composition usually hardens in a few seconds to several tens of seconds. Since it can be hardened in a short time as described above, it is possible to improve the productivity of the obtained water-repellent assembly and functional wall panel. The thickness of the coating layer can be appropriately selected depending on the desired pattern and chemical resistance, and is not particularly limited, but is usually expected to be in the range of 1 μm to 200 μm. Further, in the case of ultraviolet irradiation, since the ultraviolet curing reaction is a radical reaction, it is easily blocked by oxygen. Therefore, after the photocurable composition is applied to a substrate, the composition is cured in a nitrogen atmosphere in order to avoid contact with oxygen. Further, from the viewpoint of sufficiently ensuring good water repellency and water slidability, the surface free energy of the coating layer formed by photohardening 26 201248321 is usually 12 to 30 mJ/m 2 . Preferably, the coating layer has a rolling angle of 4 〇pL water droplets of 4 Å. Below, it is better to be 20 or less. If the 3 〇pL water droplets of the coating layer have a roll angle of 40. The following 'water' will be easy to remove from water-dispensing components and functional siding/monthly. Here, in order to make the falling angle of the water drop to 4 。. In the following, it is preferred that the compound represented by the above formula (A) (I) and the above (9) compound have a negative enthalpy & (A/D) of 0.2 to 1 Å. Also, in order to make the drop angle of the water drop to be 20. In the following, it is preferred that the mass ratio (A/D) of the compound represented by the chemical formula (1) (A) and the (D) fluorine-containing compound is 0.4 to 5.0. «Substrate layer>> The material of the substrate layer used in the water-repellent component and the functional wallboard of the present invention is exemplified by inorganic materials such as slate, concrete, metal, tannic acid, calcium carbonate, glass, etc.; Organic materials other than materials such as polypropylene, polystyrene, polycarbonate, unsaturated polyester resin; and composite materials thereof. Among them, a material obtained by adding fibers such as glass fibers and carbon fibers to an organic material, that is, a so-called FRP (fiber reinforced plastic) is preferred. The FRP is exemplified by a sheet molding compound (SMC) containing an unsaturated polyester resin, a filler, and a glass fiber or carbon fiber sheet, or a bulk BMC (bulk) which is a composite material similar to SMC and contains short fibers. Molding compound, block forming material, etc. In general, FRP is added with a thermosetting resin, an organic oxide 27 201248321 oxide (hardener), a filler, a low shrinkage agent, an internal mold release agent, a reinforcing material, a crosslinking agent, and a tackifier. The upper system puts it into a mold having a δ and a specific temperature, and pressurizes it to form a shape suitable as a position for building materials. In addition, as long as it is an unsaturated polyester containing a thermosetting resin, a filler, and FRP of glass fiber or carbon fiber as a reinforcing material, the strength of the obtained water-repellent component and the functional panel as a whole can be further improved. Long-term and so on. The unsaturated polyester may be an unsaturated acid of a polybasic acid such as maleic anhydride or fumaric acid, and ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, propylene glycol, tridecyl pentanediol, neopentyl glycol, and triterpene. A polyol such as a propane monoallyl ether, a hydrogenated bisphenol or a bisphenol dioxypropyl ether is produced. Examples of the filler include calcium carbonate, aluminum hydroxide and the like. From the viewpoint of reducing the cost, calcium carbonate is preferred, but from the viewpoint of improving the chemical resistance of FRp itself, aluminum hydroxide is preferred. However, if the coating layer is formed as described above, even if carbonic acid-FRP is used as the filler for the filler, the chemical resistance of the water-repellent assembly and the entire functional panel can be sufficiently improved, so that it can be easily A water-repellent component and a functional siding having a low-cost FRp (four) substrate layer are realized. The length of the ruthenium and the ruthenium-dimension of the reinforced material is about 2 〇 to 5 〇 mm, and the fiber diameter of about 5 to 25 μm is preferably used, and it is desirable that the FRP contains 1 〇 to 7 〇 mass%. The FRP having a specific thickness and size is produced by using the FRPH as the above-mentioned base material layer, and the like, and the FRP manufacturing apparatus 28 201248321 or the like. Further, although the thickness of the base material layer is changed by the use of the water-repellent assembly and the functional wall panel, it is usually 2.5 mm or more. The upper limit of the thickness is not particularly limited and may be appropriately selected. EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the invention should not be construed as limited. <Preparation and evaluation of photopolymerizable composition> According to the formulation shown in Tables 1 to 3, each component was poured into a mixing device and mixed to prepare a photopolymerizable composition. The obtained photopolymerizable composition was applied onto a substrate composed of FRP (DECKMAT (registered trademark) 2415' DIC Chemical Co., Ltd.) to a thickness of 2 μm. Then, UV irradiation (500 mW/cm2 '300 mJ/cm2) was carried out in an atmosphere having an oxygen concentration of 5 〇〇〇 ppm to cure the photocurable resin composition to prepare an evaluation sample. For the sample to be produced, in order to confirm the dyeability of the hair dye, the following method was used to evaluate the roll angle and the degree of soiling difficulty in the use environment, and the results shown in Table 丨 to Table 3 were obtained. Further, as a reference, after evaluating the roll-off angle of the pET film and the FRp (iron-strength plastic) plate, the results shown in Table 4 were obtained. (1) Rolling angle α The measurement of the roll-off angle was performed by Concord Interface Science Co., Ltd. DM-500 and DM-SA. A water droplet of 30 μl was dropped on the substrate, and the pedestal was tilted at a speed of 7.5 degrees/second, and the angle at which the water droplet started to move was used as the value of the angle of attack. The measurement system was performed twice, and the average value of 29 201248321 was taken as the value of the Langluo angle. (2) Dyeability The sample was immersed in a commercially available hair dye (GATSBY Back Black Hair (registered trademark): a mixture of 1 dose and 2 doses, manufactured by MANDOM Co., Ltd.), and washed with water 24 hours later. For the degree of change, a color difference meter (SpectroEye, SAKATA INX ENG) was used to determine the Lab color difference (ΔΕ) between the impregnated portion and the unimpregnated portion according to the following formula. AE=(Aa2+Ab2+AL2)1/2 The smaller the value, the better the resistance to chemicals. △ E = less than 3.0 : ◎ △ E = 3.0 or more, less than 5.0 : 〇 △ E = 5.0 or more, less than 10.0 : △

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Claims (1)

201248321 VII. Patent application scope: 1. A photopolymerizable composition comprising: (A) a compound represented by the following chemical structural formula (I): [Qi^Si-0 ch3 Si-0I ch3 ch3 Si- 0-I Rl R2 I 〇—C —C =01Si(CH3)3 • · -(1) where R2 is a hydrogen atom or a fluorenyl group, n is an integer from 1 to 20, and R1 is used to Any of the organic groups of the propyl group-introducing side bond 'm is selected from any number of the compound having a weight average molecular weight of from 1000 to 40000; (B) capable of polymerizing with the compound represented by the above chemical formula (I) a photopolymerizable oligomer and/or a photopolymerizable monomer; and (C) a photopolymerization initiator. 2. The photopolymerizable composition of claim 1, further comprising (D) a gas-containing compound. 3. The photopolymerizable composition of claim 2, wherein the mass ratio (A/D) of the compound represented by the chemical formula (1) (A) and the (D) fluorine-containing compound is 0.2. ~10.0. 4. The photopolymerizable composition of claim 3, wherein the mass ratio (A/D) of the compound represented by the chemical formula (1) (A) and the (D) fluorine-containing compound is 0.4. ~5.0. 37 201248321 5 · The photopolymerizable composition of the first aspect of the patent specification, wherein the content of the compound represented by the chemical formula (1) (A) is a photopolymerizable oligomer and light. When the total amount of the polymerizable monomer is 1 enamel, it is 0.01 to 5 mass. /〇. . 6. The photopolymerizable composition of the second or second aspect, wherein the content of the (D) fluorine-containing compound is 100% by mass of the (B) photopolymerizable oligomer and the photopolymerizable monomer. When, 〇~5 quantity%. </ RTI> </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; 8. The photopolymerizable composition of claim i, wherein the photopolymerizable monomer has a solubility parameter (S]p value of 20.0 (J/cm 3 ) ° 5 or less. '', 9. The photopolymerizable composition of claim 1 or 8', wherein the photopolymerizable monomer is a monomer represented by the following formula (II): Formula (II): (ch2=cr3coo Pr4 wherein R3 is a hydrogen atom or a methyl group, R4 is a p-valent hydrocarbon group having a carbon number of 5 to 2 Å, and P is an integer of 1 to 4. 10. A water-repellent component having the id term of the patent application range a coating layer formed by curing a photopolymerizable composition of the present invention, and a substrate layer. 11. A functional wall panel having photopolymerization according to any one of the application patents The composition of the coating 38 201248321 layer and the substrate layer formed by the hardening of the composition. 201248321 III. English Abstract: No. 4. Designated representative figure: (1) The representative representative of the case is: No. (2) Representative figure Brief description of the components and symbols: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: (CHg^Si-O ch3 Si-0 CH 3 Jn 〇i3 Si-0- I Rl R2I I OCC =CH2 Si((H3)3 • · · (I)