Compound and surface treatment agent comprising same

Abstract

The present invention relates to a novel compound represented by chemical formula 1, and to a surface treatment agent comprising same.

Description

Compound and surface treatment agent containing the same

[0001] The present invention relates to a compound represented by chemical formula 1 and a surface treatment agent comprising the same.

[0002] Perfluorinated compounds (PFCs) are widely used in everyday life, including coatings, semiconductor cleaners, food packaging, cosmetics, and herbicides. They are also emitted during distribution and manufacturing processes in various industries. However, these perfluorinated compounds do not break down during disposal, so they persist in the environment for long periods of time, potentially causing harmful effects on the human body.

[0003] Korean Patent Publication No. 10-2084270 discloses a polymer-modified silane containing a fluorooxyalkylene group capable of forming a water- and oil-repellent layer with excellent heat resistance, a surface treatment agent comprising the silane and / or a partial hydrolysis-condensation product thereof, and an article treated with the surface treatment agent. The silane has a specific structure, and the modified silane contains a fluorooxyalkylene group. However, the modified silane compound having the above structure contains a linear fluorooxyalkylene group, i.e., a perfluorinated compound structure, and thus is difficult to decompose and may be harmful to the environment and the human body. Therefore, there is a growing need for a material that can replace a perfluorinated compound while exhibiting the same performance and having excellent durability, and a surface treatment agent containing the same.

[0004]

[0005] The present invention aims to solve the above-described problems by providing a novel compound that does not contain a perfluorinated or perfluorinated compound substituent.

[0006] In addition, the present invention aims to provide a surface treatment agent that can improve wear resistance, fingerprint resistance, and / or chemical resistance when treating the surface of a substrate while reducing harmfulness to the environment and / or human body by including the novel compound and having excellent decomposability.

[0007] However, the problems to be solved by the present invention are not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

[0008]

[0009] The present invention relates to a compound represented by the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] (In the above chemical formula 1, A is each independently a substituted or unsubstituted hydrocarbon group, a hydrogen atom, or a fluorine atom, at least one of which includes a fluorine atom, B is a substituted or unsubstituted hydrocarbon group including one or more silane functional groups, l represents an integer selected from 0 to 3, m represents an integer selected from 0 to 3, at least one of l or m is 1 or more, and n represents an integer selected from 1 to 10.)

[0013] In the present invention, the silane functional group of the compound represented by the above chemical formula 1 may be at least one selected from aminosilane, epoxysilane, vinylsilane, methacryloxysilane, sulfursilane, ureidesilane, alkylsilane, alkoxysilane, alkylalkoxysilane, phenylsilane, oximesilane, isocyanatesilane, fluorosilane, and hexamethyldisilazane.

[0014] In the present invention, the silane functional group of the compound represented by the above chemical formula 1 may be an alkylsilane group, an alkoxysilane group, or an alkylalkoxysilane group.

[0015] In the present invention, each A of the compound represented by the above chemical formula 1 is independently a hydrogen atom or a fluorine atom, and may include at least one fluorine atom.

[0016] The present invention is produced by copolymerizing a compound represented by the above chemical formula 1 with a fluorobenzene-based compound and a compound containing a silyl group, and the copolymerization may be performed at a ratio of 100:5 to 100:30 with respect to the total molecular weight of monomers used in the polymerization of the copolymer of the fluorobenzene-based compound and the compound containing a silyl group.

[0017] In the present invention, the total molecular weight of the monomer used for polymerization of the compound represented by the above chemical formula 1 may be 2000 to 5000 g / mol.

[0018] In the present invention, B of the compound represented by the above chemical formula 1 may include one or more atoms selected from O, N, S, C, and Si.

[0019] In the present invention, the compound represented by the above chemical formula 1 may be one of the compounds represented by the following chemical formulas 2 to 4.

[0020] [Chemical Formula 2]

[0021]

[0022] [Chemical Formula 3]

[0023]

[0024] [Chemical Formula 4]

[0025]

[0026] (In the above chemical formulas 2 to 4, n independently represents an integer selected from 1 to 10.)

[0027] The present invention may be characterized in that the compound represented by the above chemical formula 1 does not contain a perfluorinated substituent.

[0028] Additionally, the present invention may relate to a surface treatment agent comprising the compound.

[0029] In the present invention, the surface treatment agent may further include a solvent.

[0030]

[0031] The novel compound according to the present invention does not contain a perfluorinated substituent in the molecule, and thus has excellent degradability and can reduce the impact on the environment and the human body.

[0032] When treating the surface of a substrate using a surface treatment agent including a compound according to the present invention, wear resistance, fingerprint resistance, and / or chemical resistance can be improved.

[0033]

[0034] The present invention relates to a compound for replacing a perfluorinated compound and a surface treatment agent containing the same.

[0035] Specifically, the present invention relates to a compound represented by the following chemical formula 1 and a surface treatment agent comprising the same.

[0036] [Chemical Formula 1]

[0037]

[0038] In the above chemical formula 1, A is, each independently, a substituted or unsubstituted hydrocarbon group, a hydrogen atom, or a fluorine atom, and at least one must contain a fluorine atom. B is a substituted or unsubstituted hydrocarbon group containing one or more silane functional groups. In addition, l represents an integer selected from 0 to 3, m represents an integer selected from 0 to 3, at least one of l or m is 1 or more, and n represents an integer selected from 1 to 10.

[0039] More specifically, the compound represented by the above chemical formula 1 may be a silane compound which is a copolymer of a fluorobenzene ester compound and a compound containing a silyl group, and is characterized in that it does not contain a perfluorinated substituent, preferably a straight-chain perfluorinated substituent, more preferably a perfluorinated methyl group (-CF3) and / or a perfluorinated methylene group (-CF2-).

[0040] The novel compound of the present invention is characterized by solving the problem of recalcitrance to decomposition of perfluorinated compounds by including a fluoro group (F, fluorinated group) in the form of a fluorobenzene ester linker, thereby reducing the impact on the environment and / or the human body. In the case of the CF bond included in the existing perfluorinated compounds, it has a high bonding strength with low polarization, but in the case of the bond between the carbon of the benzene ring of the compound represented by the chemical formula 1 of the present invention and the fluorine atom A (for convenience, referred to as “C=F bond”), it has a higher possibility of decomposition by reacting with oxygen with a lower bonding strength than the CF bond.

[0041] In addition, in the present invention, the surface treatment agent including the compound represented by the chemical formula 1 may have improved wear resistance, fingerprint resistance, and / or chemical resistance.

[0042]

[0043] Hereinafter, embodiments of the present invention will be described in more detail. The terms used herein are for the purpose of describing embodiments and are not intended to limit the present invention.

[0044] As used herein, the terms 'comprises' and / or 'comprising' are used to mean that they do not exclude the presence or addition of one or more other components and / or ingredients other than the mentioned components and / or ingredients.

[0045]

[0046] <Compound represented by chemical formula 1>

[0047] The compound of the present invention may be a fluorobenzene ester silane compound, and specifically, a compound represented by the following chemical formula 1.

[0048] [Chemical Formula 1]

[0049]

[0050] In the above chemical formula 1, each A is independently a substituted or unsubstituted hydrocarbon group, a hydrogen atom, or a fluorine atom, and at least one of the A's must contain a fluorine atom. B is a substituted or unsubstituted hydrocarbon group containing one or more silane functional groups. l represents an integer selected from 0 to 3, m represents an integer selected from 0 to 3, at least one of l or m must be 1 or greater, and n represents an integer selected from 1 to 10. Preferably, the A's are a hydrogen atom or a fluorine atom, and at least one of the A's may be a fluorine atom. Most preferably, all of the A's are fluorine, which is advantageous in achieving the purpose of the present invention. In addition, preferably, the B may be a hydrocarbon group having 2 to 20 carbon atoms including one or two silane functional groups, the l may represent an integer selected from 1 to 2, the m may represent an integer selected from 0 to 1, and the n may represent 1.

[0051] The compounds A represented by the above chemical formula 1 each independently contain one or more fluorine atoms, thereby having the technical advantages of low surface energy, thermal stability, and good solubility in solvents. In addition, the compounds A represented by the above chemical formula 1 each independently may further contain one or more substituents selected from among substituents that may be included in the present technical field without limitation.

[0052] Compound B represented by the above chemical formula 1 has an advantage in that the silane functional group includes both an organic functional group and an inorganic functional group, so that the coating property is excellent and, when applied to a composite material, it is advantageous in terms of improved mechanical strength and / or durability. The silane functional group may refer to all substituents including a conventional silane group, and may be a substituent derived from at least one selected from silanes linked to a nitrogen atom, such as aminosilane, epoxysilane, vinylsilane, methacryloxysilane, sulfursilane, ureidesilane, alkylsilane, alkoxysilane, alkylalkoxysilane, phenylsilane, oximesilane, isocyanatesilane, fluorosilane, and hexamethyldisilazane. In the present invention, the "derived substituent" may mean a substituent in which at least one hydrogen is removed from the structure of the compound, or a substituent including the same. According to one embodiment of the present invention, the silane functional group is preferably derived from an alkylsilane, an alkoxysilane and / or an alkylalkoxysilane, more preferably derived from an alkylsilane having 2 to 20 carbon atoms, an alkoxysilane having 1 to 10 carbon atoms, and / or an alkyl (having 1 to 10 carbon atoms) alkoxysilane (having 2 to 20 carbon atoms), and in particular, n-Propyltriethoxysilane, n-Propyltrimethoxysilane, n-Octyltriethoxysilane, n-Octyltrimethoxysilane, n-Dodecyltrimethoxysilane, A substituent derived from n-hexadecyltrimethoxysilane and / or tetraethoxysilane is preferable in that it has excellent processability when coated on synthetic glass and can form a dipodal.

[0053] The compound B represented by the above chemical formula 1 may include a silane functional group and further include one or more atoms selected from O, N, S, C, and Si within the structure. Since the above atoms can form a dipodal of the silane group, the fluorine moiety can stand perpendicular to the substrate immediately after the compression reaction between the substrate and the silane group. More preferably, in order to achieve the purpose of the present invention, the silane functional group may have a structure in which the mother nucleus of the compound represented by the chemical formula 1 is connected by -O-, -N=, and / or -S-, etc.

[0054]

[0055] The compound of the above chemical formula 1 may be manufactured by copolymerizing a fluorobenzene-based compound and a compound containing a silyl group, but is not limited thereto. For example, according to one embodiment of the present invention, after synthesizing poly(hexaflourophenol) and / or 2,3,5,6-tetrafluoro-4-((perfluoro-[1,1'-biphenyl]-4-yl)oxy)phenol, a material corresponding to the compound represented by the chemical formula 1 of the present invention may be manufactured by copolymerizing each of the above fluorobenzene-based compounds with 3-chloropropylmethoxysilane or the like. The compound represented by the chemical formula 1 of the present invention can be copolymerized with a fluorobenzene-based compound and a compound containing a silyl group at a ratio of 100:5 to 100:30, preferably 100:5.5 to 100:15, based on the total molecular weight of monomers used for polymerization of the copolymer. In addition, the total molecular weight of the monomers used for polymerization of the compound represented by the chemical formula 1 is preferably 2000 to 5000 g / mol. If the molecular weight is 2000 g / mol or less, wear resistance is reduced due to insufficient fluorine, and if it is 5000 g / mol or more, it may become insoluble due to the high molecular weight.

[0056] The above fluorobenzene compound may be one in which hydrogen in the benzene group is replaced by a substituted or unsubstituted hydrocarbon group, a hydrogen atom, or a fluorine atom, and at least one or more must be substituted by a fluorine atom. In addition, it may be linked by an ester group, and for example, it may be one represented by the following chemical formula A, which is a fluorobenzene ester compound.

[0057] [Chemical Formula A]

[0058]

[0059] In the above chemical formula A, n may be an integer selected from 1 to 10.

[0060] The compound containing the above silyl group contains a silane functional group, and the silane functional group is the same as described above, but is not limited thereto.

[0061] The method for producing the above copolymer is not particularly limited. For example, methods commonly used in the technical field to which the present invention pertains, such as bulk polymerization, solution polymerization, emulsion polymerization, suspension polymerization, or UV polymerization, may be used. Preferably, solution polymerization or UV polymerization may be used.

[0062]

[0063] More specifically, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formulas 2 to 4.

[0064] [Chemical Formula 2]

[0065]

[0066] [Chemical Formula 3]

[0067]

[0068] [Chemical Formula 4]

[0069]

[0070] In the above chemical formulas 2 to 4, n may represent an integer selected from 1 to 10.

[0071]

[0072] Surface treatment agent

[0073] The present invention encompasses a surface treatment agent comprising a compound represented by the above-described chemical formula 1. The surface treatment agent may be used in the form of a surface treatment agent composition by further including a solvent in the above-described chemical formula 1. In addition, the surface treatment agent may be used by vacuum-treating, drying, applying, and / or curing the surface of a substrate.

[0074] The above surface treatment agent is characterized by improved durability, such as application properties and wear resistance, fingerprint resistance, and / or chemical resistance.

[0075]

[0076] Compound represented by chemical formula 1

[0077] The compound represented by chemical formula 1 included in the surface treatment agent of the present invention can be applied as is to the above-described compound, so description thereof will be omitted.

[0078]

[0079] solvent

[0080] The solvent is not limited to any solvent known to be usable in compositions of the present technical field, as long as it can dissolve or disperse the compound represented by Chemical Formula 1. For example, usable solvents include fluorinated solvents (hydrofluoroether, perfluorohexylethyl alcohol, perfluoroether, perfluorohexane, etc.). Alcohols (methanol, ethanol, isopropanol, butanol, methyl cellusob, ethylsolusob, etc.), ketones (methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, diethyl ketone, dipropyl ketone, cyclohexanone, etc.), acetates (ethyl acetate, propyl acetate, normal butyl acetate, tert-butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, methoxypentyl acetate, etc.), hexane (hexane, heptane, octane, etc.), benzene (benzene, toluene, xylene, etc.), ethers (diethylene glycol dimethyl ether, diethylene glycol diethyl ether, Diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, etc.) and the above-mentioned solvents may be used alone or in combination of two or more, but are not limited thereto. However, in one embodiment of the present invention, it is more preferable to use a fluorinated solvent because it increases solubility with fluorinated compounds and lowers the coefficient of friction, thereby enhancing slipperiness. Examples of the fluorinated solvent include hydrofluoroether, perfluorohexylethyl alcohol, perfluoroether, and / or perfluorohexane.

[0081]

[0082] According to one embodiment of the present invention, the solvent may be included in an amount such that the concentration of the compound represented by Chemical Formula 1 is 0.1 to 50 wt%, and preferably 0.1 to 25 wt%. Specifically, the "remaining amount" in the present invention means the remaining amount such that the total weight of the composition further including the essential components of the present invention and other additional components becomes 100 wt%, and the meaning of the "remaining amount" is not limited to the surface treatment composition of the present invention not including additional components. For example, the solvent may be included in an amount of 30 to 99.9 wt%, and preferably 50 to 99.9 wt%, based on the total weight of the surface treatment composition. When the solvent is in the above-mentioned range, it provides an effect of improving the applicability when deposited on a glass surface.

[0083]

[0084] etc

[0085] In order to provide the surface treatment agent of the present invention, in addition to including the above-described compound, any composition commonly used for producing a surface treatment agent in the same field can be used without limitation.

[0086] The surface treatment agent of the present invention can be applied to the surface of a substrate such as paper, cloth, metal and its oxide, glass, plastic, ceramic and / or quartz to impart wear resistance, fingerprint resistance, chemical resistance, etc., and can be effectively used as a surface treatment agent for treating a glass surface in particular.

[0087] The surface treatment agent of the present invention can be applied using any manufacturing method commonly used to produce surface treatment agents in the field without limitation. The application can generally be performed by a knife coater, roll coater, calendar coater, comma coater, brush application, dipping, spraying, or deposition treatment. Additionally, depending on the application thickness or viscosity of the surface treatment agent composition, the application can be performed by a gravure coater, rod coater, or the like.

[0088] The thickness of the surface treatment agent excluding the substrate is not particularly limited, but may be formed to be 1 to 50 ㎛, preferably 1 to 30 ㎛, and more preferably 1 to 15 ㎛ in terms of wear resistance and / or antifouling properties.

[0089]

[0090]

[0091] Hereinafter, experimental examples including specific examples and comparative examples are presented to help understand the present invention, but these are only illustrative of the present invention and do not limit the scope of the appended claims. It will be apparent to those skilled in the art that various changes and modifications to the examples are possible within the scope and technical idea of ​​the present invention, and it is natural that such changes and modifications fall within the scope of the appended claims. “%” and “parts” in the examples mean “mass%” and “mass parts”, respectively, unless otherwise specified.

[0092]

[0093] < Synthetic example >

[0094] Synthesis Example 1: Polyfluorobenzyl ester silane compound represented by chemical formula a

[0095] (1) Synthesis step of poly(hexaflourophenol) of chemical formula a-1

[0096] Tetrafluorophenol (9.30 g, 0.05 mol) and potassium hydroxide (16.79 g, 0.3 mol) were added to dimethyl sulfoxide (150 ml), and the mixture was stirred at 100°C for 24 hours after nitrogen purging. After completion of the reaction, deionized water (100 ml) was added, and the organic phase was separated and extracted with ethyl acetate. After removing moisture from the organic phase with sodium sulfate, it was filtered and dried to obtain 12.15 g of compound of chemical formula a-1. (Weight average molecular weight: 3400 g / mol)

[0097] [Chemical formula a-1]

[0098]

[0099]

[0100] (2) Synthesis step of fluorobenzene ester silane compound of chemical formula a

[0101] 7 g of polyfluorobenzyl ester of chemical formula a-1 obtained in (1) above, 3-chloropropylmethoxysilane, and potassium carbonate were added to dimethylformamide (100 ml), and after nitrogen purging, the mixture was stirred at 100°C for 24 hours. Thereafter, the mixture was washed with ethyl acetate and deionized water, the organic phase was separated, dried over depleted calcium hydroxide, filtered, and dried to obtain 5 g of compound of chemical formula a. (Weight average molecular weight: 3540 g / mol)

[0102] [chemical formula a]

[0103]

[0104]

[0105] Synthesis Example 2: Polyfluorobenzyl ester silane compound represented by chemical formula b

[0106] (1) Synthesis step of poly(2,3,5,6-tetrafluoro-4-(perfluorophenoxy)phenol) of chemical formula b-1

[0107] Hexafluorobenzene (9.30 g, 0.05 mol), potassium hydroxide (16.79 g, 0.3 mol), and tetrafluoroquinone (9.1 g, 0.05 mol) were added to dimethyl sulfoxide (150 ml), and the mixture was stirred at 100°C for 24 hours after nitrogen purging. After completion of the reaction, deionized water (100 ml) was added, and the organic phase was separated and extracted with ethyl acetate. The organic phase was dried with sodium sulfate, filtered, and dried to obtain 12.15 g of a compound of chemical formula b-1. (Weight average molecular weight: 3610 g / mol)

[0108] [Chemical formula b-1]

[0109]

[0110]

[0111] (2) Synthesis step of fluorobenzene ester silane compound of chemical formula b

[0112] 8 g of polyfluorobenzyl ester of chemical formula 2a obtained in (1) above, 3-chloropropylmethoxysilane, and potassium carbonate were added to dimethylformamide (100 ml), and after nitrogen purging, the mixture was stirred at 100°C for 24 hours. Ethyl ether (150 ml) was added and separated to obtain an organic phase, which was washed with deionized water. After removing moisture from the organic phase with sodium sulfate, it was filtered and dried to obtain 10.01 g of a compound of chemical formula b. (Weight average molecular weight: 3730 g / mol)

[0113] [chemical formula b]

[0114]

[0115]

[0116] Synthesis Example 3: Polyfluorobenzyl ester silane compound represented by chemical formula c

[0117] (1) Synthetic step of 2,3,5,6-tetrafluoro-4-((perfluoro-[1,1'-biphenyl]-4-yl)oxy)phenol of chemical formula c-1

[0118] Hexafluorobenzene (9.30 g, 0.05 mol), potassium hydroxide (16.79 g, 0.3 mol), and octafluoro-4,4'-biphenyl (16.70 g, 0.05 mol) were added to dimethyl sulfoxide (150 ml), and the mixture was stirred at 100°C for 24 hours after nitrogen purging. After completion of the reaction, deionized water (100 ml) was added, and the organic phase was separated and extracted with ethyl acetate. The organic phase was dried with sodium sulfate, filtered, and dried to obtain 15.23 g of a compound of the formula c-1. (Weight average molecular weight: 2820 g / mol)

[0119] [Chemical formula c-1]

[0120]

[0121]

[0122] (2) Synthesis step of polyfluorobenzyl ester compound of chemical formula c-2

[0123] 10 g of polyfluorobenzyl ester of chemical formula c-1 obtained in (1) above, trifluoromethanesulfonyl chloride, and triethylamine were added to dimethylformaldehyde (100 ml), and after nitrogen purging, the mixture was stirred at 100°C for 24 hours. Ethyl acetate (150 ml) was added and separated to obtain an organic phase, which was washed with deionized water. After removing moisture from the organic phase with sodium sulfate, it was filtered and dried to obtain 11.17 g of a compound of chemical formula c-2. (Weight average molecular weight: 3010 g / mol)

[0124] [Chemical formula c-2]

[0125]

[0126]

[0127] (3) Synthesis step of fluorobenzene ester silane compound of chemical formula c

[0128] 10 g of polyfluorobenzyl ester of chemical formula c-2 obtained in (2) above, bis(3-trimethoxysilylpropyl)amine, and potassium carbonate were added to dimethylformaldehyde (100 ml), and after nitrogen purging, the mixture was stirred at 100°C for 24 hours. Ethyl ether (150 ml) was added and separated to obtain an organic phase, which was washed with deionized water. After removing moisture from the organic phase with sodium sulfate, it was filtered and dried to obtain 8.70 g of a compound of chemical formula c. (Weight average molecular weight: 3100 g / mol)

[0129] [chemical formula c]

[0130]

[0131]

[0132] <Examples and Comparative Examples>

[0133] Example 1

[0134] Compound a obtained in the above Synthesis Example 1 was dissolved in hydrofluoroether (Novec HFE7200, manufactured by 3M Corporation) to a concentration of 20 wt% to prepare a surface treatment agent 1. The surface treatment agent 1 prepared above was vacuum-deposited on chemically strengthened glass (Corning Corporation, "Gorilla" glass, thickness 0.7 mm). The treatment conditions for vacuum deposition were a pressure of 3.0 X 10 -3 ㎩, and a 7 nm silicon dioxide film was formed on the surface of chemically strengthened glass, and then 2 mg of a surface treatment agent (i.e., containing 0.4 mg of compound a) was deposited per sheet of chemically strengthened glass (55 mm X 100 mm). Thereafter, the chemically strengthened glass having the deposited film was cured for 24 hours in an atmosphere of 20°C and 65% humidity.

[0135]

[0136] The physical properties of the manufactured adhesive sheet were measured using the following method, and the results are shown in Table 1 below.

[0137]

[0138] Example 2

[0139] A surface treatment agent 2 was prepared in the same manner as in Example 1, except that the compound of chemical formula b obtained in Synthesis Example 2 was used instead of Compound A, and an adhesive sheet of Example 2 with a surface treatment layer formed thereon was produced.

[0140]

[0141] Example 3

[0142] In the same manner as Example 1, except that the compound of chemical formula c obtained in Synthesis Example 3 was used instead of Compound A, a surface treatment agent 3 was prepared, and Example 3 was produced in which a surface treatment layer was formed.

[0143]

[0144] Comparative Examples 1 to 3

[0145] Surface treatment agents 4 to 6 were prepared in the same manner as in Example 1, except that the following control compounds 1 to 3 were used instead of compound a, and Comparative Examples 1 to 3 were produced, each forming a surface treatment layer.

[0146] [Control compound 1]

[0147] CF3O(CF2CF2O)20(CF2O) 16 CF2CH2OCH2CH2CH2Si(OCH3)3

[0148] [Control compound 2]

[0149] CF3O(CF2CF2O)20(CF2O) 16 CF2CH2OCH2CH2CH2Si[CH2CH2CH2Si(OCH3)3]3

[0150] [Control compound 3]

[0151] CF3O(CF2CF2O)20(CF2O) 16 CF2CH2OCH2CH2C[CH2CH2Si(OCH3)3]3

[0152]

[0153] <Experimental Example>

[0154] Experimental Example: Friction Durability Evaluation

[0155] For the surface treatment layer formed on the substrate surface in the above examples and comparative examples, the static contact angle of water was measured. The static contact angle of water was measured using a contact angle measuring device (manufactured by Kyowa Kaimen Kagaku Co., Ltd.) with 1 μL of water.

[0156] First, as an initial evaluation, after the formation of the surface treatment layer, the static contact angle of water was measured when the surface was not yet in contact with anything (number of friction cycles: 0). Then, as an evaluation of friction durability, a steel wool friction durability evaluation was conducted. Specifically, the substrate on which the surface treatment layer was formed was placed horizontally, steel wool (count #0000, dimensions 5mm X 10mm X 10mm) was brought into contact with the exposed upper surface of the surface treatment layer, a load of 1,000 gf was applied thereto, and then the steel wool was reciprocated at a speed of 140 mm / s while the load was applied. The static contact angle (°) of water was measured every 2,500 reciprocations, and the evaluation was stopped when the measured contact angle value was less than 100°. The results are shown in Table 1 below (in the table, the symbol "-" indicates that it was not measured).

[0157] Number of wear times (times)Contact angle (°)Example 1Example 2Example 3Comparative Example 1Comparative Example 2Comparative Example 30113.8114.0114.1113114.1114.32500113.5113.3113.1104111.8111.25000113.0112.5112.274.3111.1109.07500112.5112.1110.4-108.8106. 110000111.8110.2108.1-106.4105.412500111.3108.5107.2-105.2104.215000111108.1105.7-104.5103.517500110.5105.2105.8-9910120000110.3105105.1-9722500109.1103.7103.4--

[0158] According to the experimental data in Table 1 above, in the case of the surface treatment layer manufactured using the surface treatment agent of Examples 1 to 3 of the present invention, the contact angle was maintained at 100° or more even as the number of wear increases, showing excellent wear resistance, whereas in the case of Comparative Examples 1 to 3 using the surface treatment agent not including the compound represented by Chemical Formula 1, the contact angle was easily reduced. That is, it was experimentally confirmed that when the compound represented by Chemical Formula 1 of the present invention and the surface treatment agent including it were used, the durability such as wear resistance was excellent.

[0159]

[0160] The novel compound according to the present invention does not contain a perfluorinated substituent in the molecule, and thus has excellent degradability and can reduce the impact on the environment and the human body.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, A is, each independently, a substituted or unsubstituted hydrocarbon group, a hydrogen atom or a fluorine atom, and contains at least one fluorine atom, B is a substituted or unsubstituted hydrocarbon group containing one or more silane functional groups, l represents an integer selected from 0 to 3, m represents an integer selected from 0 to 3, and at least one of l or m is 1 or greater, n represents an integer selected from 1 to 10.

2. In claim 1, A compound in which the silane functional group of the compound represented by the above chemical formula 1 is derived from at least one selected from aminosilane, epoxysilane, vinylsilane, methacryloxysilane, sulfursilane, ureidesilane, alkylsilane, alkoxysilane, alkylalkoxysilane, phenylsilane, oximesilane, isocyanatesilane, fluorosilane, and hexamethyldisilazane.

3. In claim 2, A compound in which the silane functional group of the compound represented by the above chemical formula 1 is an alkylsilane group, an alkoxysilane group or an alkylalkoxysilane group.

4. In claim 1, A compound represented by the above chemical formula 1, wherein each A is independently a hydrogen atom or a fluorine atom, and includes at least one fluorine atom.

5. In claim 1, The compound represented by the above chemical formula 1 is manufactured by copolymerizing a fluorobenzene compound and a compound containing a silyl group. A compound in which the above fluorobenzene compound and the compound containing a silyl group are copolymerized at a ratio of 100:5 to 100:30 with respect to the total molecular weight of monomers used for polymerization of the copolymer.

6. In claim 5, A compound having a total molecular weight of monomers used in the polymerization of the compound represented by the above chemical formula 1 of 2000 to 5000 g / mol.

7. In claim 1, Compound B represented by the above chemical formula 1 is a compound including at least one atom selected from O, N, S, C, and Si in its structure.

8. In claim 1, The compound represented by the above chemical formula 1 is one of the compounds represented by the following chemical formulas 2 to 4: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 2 to 4, n represents an integer selected independently from 1 to 10.

9. In claim 1, A compound represented by the above chemical formula 1, characterized in that it does not contain a perfluorinated substituent.

10. A surface treatment agent comprising a compound according to any one of claims 1 to 9.

11. In claim 10, A surface treatment agent containing a solvent.

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