KR100959850B1 - Surface Treating Compound And Method Forming Coating Layer Including The Same - Google Patents

Abstract

A novel surface treatment compound and a method of forming an antifouling coating film are disclosed that are applied to form an antifouling coating film. The surface treating compound includes a perfluoropolyether-modified polyalkylether silane represented by the following general formula (1) or a partial hydrolysis condensation product of the perfluoropolyether-modified polyalkylether silane. Therefore, by using a surface treating agent containing such a surface treating compound, a coating film having excellent antifouling property, internal adhesion, and durability may be formed on the surface of the object.

[ Formula 1 ]

Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂

Description

Surface Treating Compound And Method Forming Coating Layer Including The Same}

The present invention relates to a surface treatment compound and a method for forming a coating film including the same, and more particularly, to a surface treatment compound including a novel modified perfluoropolyether-modified polyalkyl ester silane and a coating film formation method including the same.

In general, perfluoropolyether-containing compounds have physical properties such as water and oil repellency, chemical resistance, lubricity, mold release and antifouling properties due to their very low surface energy. Because of these properties, perfluoropolyether-containing compounds are widely used to form protective coating films for water and oil repellent antifouling agents for paper and textiles, lubricants for magnetic recording media, oil repellents for precision machinery, mold release agents, cosmetic raw materials, and light-resistant materials. have. However, general perfluoropolyether-containing compounds having such characteristics have weak adhesion and weak adhesion to the substrate, and thus it is difficult to form a rigid coating film firmly bonded to the substrate.

In contrast, silane coupling agents are widely known as a means of establishing a tight bond between the surface of a material, such as glass or cloth, and an organic compound. The silane coupling agent has organic functional radicals and reactive silyl radicals (typically alkoxysilyl radicals) in the molecule, the alkoxysilyl radicals undergo a self-condensation reaction with moisture in the air to form a coating. . At the same time, the silane coupling agent can form chemical and physical bonds with the glass or metal surface to form a rigid coating film having durability. Therefore, in recent years, perfluoropolyester-modified silane compounds which utilize the low surface energy of perfluoropolyether and use the adhesion ability of the silane coupling agent to various substrates have been used as surface treatment agents having antifouling functions. have.

A perfluoropolyester-modified silane compound of formula (6) applied to a surface treatment agent having the above-mentioned characteristics is disclosed in Japanese Patent Application Laid-Open No. JP1998-167597.

Rf [(CH ₂ ) _n -O- (CH ₂ ) _m -Si (R _3-a ) X _a ] ₂ -------

(In the formula, Rf divalent linear perfluoropolyether, R is a C1-C4 alkyl group or phenyl group, X is an organooxy group, n is an integer of 0 to 2, m is an integer of 1 to 5, a Is 2 or 3)

However, the perfluoropolyester-modified silane compound of the above formula is excellent in adhesion to the substrate, but lacks durability against the environment such as continuous friction from the outside, continuous contact with salt water, constant temperature and humidity, This is difficult to apply.

Accordingly, a first object of the present invention for solving the above problems is to provide a novel surface treatment compound having a perfluoropolyether functional group capable of sufficiently ensuring the adhesion to the substrate.

In addition, a second object of the present invention is to provide a method of forming a coating for preventing contamination containing the surface treatment compound.

The novel surface treatment compound according to an embodiment of the present invention for achieving the above object is a perfluoropolyether-modified polyalkyl ether silane represented by the following formula (1), the perfluoropolyether-modified polyalkyl ether Partial hydrolysis condensates of silanes or mixtures thereof.

Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂ ------ [Formula 1]

In Formula 1, Rf is a linear or branched perfluoropolyether group whose divalent terminal is not an oxygen atom. In Formula 1, m is an integer of 1 to 3, n is an integer of 1 to 5. In Formula 1, a is an integer of 1 to 3, R is a lower alkyl or phenyl group having 1 to 4 carbon atoms, and X is an oxyalkyl or acetoxy group having 1 to 3 carbon atoms as a hydrolysis reactor.

In Formula 1, Rf includes a perfluoropolyether repeating unit having 1 to 4 carbon atoms, and satisfies the number average molecular weight of 800 to 9000.

In order to form a coating film according to an embodiment of the present invention for achieving the second object, first to provide a surface treatment agent for forming a coating film containing a surface treatment compound and an extra solvent. Subsequently, a contamination prevention coating film containing the surface treating compound as a main component is formed on the surface of the object to be treated. Wherein the surface treatment compound comprises a perfluoropolyether-modified polyalkylether silane represented by Formula 1, a partial hydrolysis condensation product of the perfluoropolyether-modified polyalkylether silane, or a mixture thereof It features.

For example, the coating film may be formed on the object to be processed by performing a vacuum deposition method or a wet coating method.

As described above, the novel surface treatment compound represented by Chemical Formula 1 of the present invention is useful for forming an antifouling coating film having low surface energy and minimized adhesion to contaminants and excellent durability. Therefore, the antifouling coating film mainly composed of the new surface treatment compound can maintain the antifouling effect against contaminants in the long term, and easily wipe off the contaminants even when the contaminants are attached and deteriorate the function by rubbing. Or damage to its surface can be minimized.

Hereinafter, preferred embodiments of the present invention will be described in detail so that those skilled in the art may easily implement the technical idea of the present invention. However, the present invention is not limited to the embodiments described herein and may be implemented in various forms. Rather, the embodiments disclosed herein are provided to enable the spirit of the present invention to be thorough and complete, and to fully convey the spirit of the present invention to those skilled in the art.

Surface treatment compounds

The surface treatment compound applied to the formation of the antifouling coating film according to the present invention is a perfluoropolyether-modified polyalkyl ether silane represented by the following general formula (1). As another example, the surface treatment compound is a partial hydrolysis condensation product of the perfluoropolyether-modified polyalkylether silane represented by Chemical Formula 1. As another example, the surface treatment compound includes both the perfluoropolyether-modified polyalkylether silane represented by Formula 1 and partial hydrolysis condensates thereof.

Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂ ____________ [Formula 1]

In Formula 1, Rf is a linear or branched perfluoropolyether group whose divalent terminal is not an oxygen atom, m is an integer of 1 to 3, n is an integer of 1 to 5, wherein a is It is an integer of 1-3, R is a C1-C4 lower alkyl group or a phenyl group, X is a hydrolysable group and C1-C3 oxyalkyl or acetoxy group.

Specifically, the perfluoropolyether represented by Rf includes repeating units of perfluoropolyether having about 1 to about 4 carbon atoms, and the perfluoropolyether has a number average molecular weight of about 800 to 9000. Satisfies. As an example, the divalent linear perfluoropolyether represented by Rf may be represented by the following Chemical Formula 2, the following Chemical Formula 3 or Chemical Formula 4.

-CF ₂ O- (C ₂ F ₄ O) _p- (CF ₂ O) _q -CF ₂ -__________

In the perfluoropolyether represented by Chemical Formula 2, p or q satisfy 1 to 100, respectively, preferably p / q is 0.2 to 2, and p + q satisfies 40 to 180.

-C ₂ F ₄ O- (C ₃ F ₆ O) _r- (CF ₂ O) _s -C ₂ F ₄ - _{_} _________

In the perfluoropolyether represented by the formula (3), the r or s satisfies 1 to 100, preferably r / s is 0.2 to 2, r + s to 40 to 180.

-C ₂ F ₄ O- (C ₃ F ₆ O) _t -C ₂ F ₄ -_________________

In the perfluoropolyether represented by the formula (4), t is 1 to 100 is satisfied. Here, the molecular structure of the perfluoropolyether in the above formulas is not limited to the illustrated structure.

In addition, the perfluoropolyether-modified polyalkylether silane represented by Formula 1 includes a polyalkylether functional group. Examples of the polyalkyl ether functional group include polymethylene oxide, polyethylene oxide, polypropylene oxide, polybutylene oxide and the like.

X is a hydrolyzable group. Examples of the hydrolyzable group include methoxy, ethoxy, propoxy, alkoxy groups such as butoxy, acyloxy groups such as acetoxy, alkenyloxy groups such as isopropenoxy and the like. R is a lower alkyl or phenyl group of 1 to 4 carbon atoms. Methyl, ethyl, etc. are mentioned as an example of the said lower alkyl group.

Although the molecular weight is not critical for the compounds of the present invention, those having a number average molecular weight of about 800 to 10,000 and suitably having a number average molecular weight of 1000 to 9,000 in consideration of stability and ease of handling. Examples of perfluoropolyether-modified silanes include, but are not limited to, those of the following structural formulas.

A feature of the present invention is that the polyalkylether functional group is located between the silane functional group and the perfluoropolyether functional group as represented by the formula (1). Thus, the perfluoropolyether functional group has non-adhesiveness and non-adherence to the polymer chain and the substrate. The polyalkyl ether functional group acting as a spacer allows the silane functional group to easily adhere to the substrate and provides a function of protecting the adhesive surface between the silane and the substrate from an external environment (chemical contact with mechanical friction, moisture, etc.). . Furthermore, the polyalkyl ether functional group provides compatibility with organic compounds (including solvents) in addition to fluorine-based compounds (including solvents), and thus can be widely used in a manner of being added to various coating surface treatment agents.

Hereinafter, the manufacturing method of the said perfluoro polyether modified polyalkyl ether silane is demonstrated.

When the perfluoropolyether-modified polyalkylether silane is prepared, a perfluoroether functional group having a functional group and a perfluoroether functional group having an allyl functional group at the sock end and / or a perfluoro having a silane functional group at the sock end Ropolyethers are used.

Examples of the perfluoroether to which the functional group is provided include the trade name of fluorolink of Solvey and the name of Krytox® of Dupont. The perfluoroether functional group having an allyl functional group on the sock end is reacted with an allylhalogen compound after reacting a polyperfluoroether whose both ends are modified with alcohol with an alkali metal hydroxide such as sodium or potassium hydroxide. Can be prepared by reaction. In addition, perfluoropolyether having a silane functional group at the sock end is generally produced by hydrosilylation reaction using a platinum-based catalyst with hydrosilane as the allyl functional group.

Surface treatment agent for coating film formation and coating film formation method using the same

The surface treatment agent used to form the antifouling coating film according to the present invention has a composition comprising the above-described surface treatment compound and a solvent.

As an example of the surface treatment compound used for the surface treating agent which has the above-mentioned composition, the perfluoropolyether modified polyalkyl ether silane represented by following General formula (1), the partial hydrolysis-condensation product of the said perfluoro polyether modified polyalkyl ether silane Or mixtures thereof. In this case, since the details of the surface treatment compound have been described in detail above, it is omitted to avoid duplication.

Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂ ____________ [Formula 1]

In addition, the solvent includes at least one solvent. It is preferable to use a solvent in which the perfluoropolyether-modified polyalkylether silane represented by Chemical Formula 1 and / or a partial hydrolysis condensate thereof can be uniformly dissolved.

Examples of the solvent include fluorine-modified aliphatic hydrocarbon solvents (perfluoroheptane and perfluorooctane), fluorine-modified aromatic hydrocarbon solvents (m-xylene hexafluoride and benzotrifluoride), fluorine-modified ether solvents (methylpurple Fluorobutylether and perfluoro (2-butyltetrahydrofuran)), fluorine-modified alkylamine solvents (perfluorotributylamine and perfluorotripentylamine), hydrocarbon solvents (petroleum benzine, mineral spirits, toluene and xylene ) And ketone solvents (acetone, methyl ethyl ketone and methyl isobutyl ketone). Among them, it is preferable to use a fluorine-modified solvent from the viewpoint of solubility and wettability.

The surface treatment agent containing the above-mentioned surface treatment compound, perfluoropolyether-modified polyalkylether silane, is coated on a target object (paper, cloth, metal, metal oxide, glass, plastic, porcelain, ceramic, etc.), It is possible to form an antifouling coating film having excellent durability. For example, the surface treating agent is useful as a surface treating agent for forming an antifouling coating film requiring contamination resistance and durability at the surface of the antireflective layer.

Hereinafter, a method of forming a coating film using the surface treating agent will be described.

First, the surface treatment agent for coating film formation containing a surface treatment compound and a solvent is prepared. The surface treatment compound included in the surface treatment may be a perfluoropolyether-modified polyalkyl ether silane represented by the following formula (1), a partial hydrolysis condensation product of the perfluoropolyether-modified polyalkyl ether silane, or a Includes a groove.

Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂ ------- [Formula 1]

In Formula 1, Rf is a linear or branched perfluoropolyether group having a bivalent terminal which is not an oxygen atom, m is an integer of 1 to 3, and n is an integer of 1 to 5, wherein a Is an integer of 1 to 3, R is a lower alkyl group or phenyl group having 1 to 4 carbon atoms, and X is an oxyalkyl or acetoxy group having 1 to 3 carbon atoms as a hydrolysis reactor.

The content of the surface treating compound contained in the surface treating agent is changed in composition depending on the method of forming the coating film. For example, when the coating film is formed by applying a vacuum deposition technique, the surface treatment agent has a composition including 10 to 70% by weight of the surface treatment compound and an extra solvent, and when the wet coating method is formed, The surface treating agent may have a composition comprising 0.001 to 5% by weight of the surface treating compound and an extra solvent.

Subsequently, a coating film containing the surface treating compound as a main component is formed on the surface of the object to be treated using the surface treating agent.

For example, the coating layer may be formed by vacuum evaporation, which comprises evaporating the surface treating compound including the surface treating agent and vacuum depositing the surface treating compound on the surface of the object to be treated (vacuum deposition by electron beam heating and Vacuum deposition by heating molybdenum boats). In particular, the vacuum deposition technique is performed by using a tablet formed by impregnating the surface treatment agent in a molded article (ceramic tablet, steel wool tablet, etc.) having voids and then evaporating the solvent contained in the surface treatment agent. The object to be treated with the coating film formed by the deposition technique is excellent in antifouling function, and no additional coating process is required.

As another example, the coating layer may be formed by performing a wet coating method (spray, immersion, gravure, etc.) including coating the surface treating agent on the surface of the object to be treated and drying the surface treating agent. .

Examples of products to which a coating film formed by using a surface treatment agent are applied to the surface of the object to be treated include optical members such as spectacle lenses and antireflection filters (coating to prevent fingerprint and fat contamination), and vehicles such as cars, trains, and aircrafts. Window panes and headlamp covers (antifouling coatings), and building exteriors (water repellent, antifouling coatings); Kitchen utensils (coating to prevent oil contamination), art works (water and oil repellent, anti-fingerprint coating), compact discs and DVDs (coating to prevent fingerprints), and the like.

In particular, the surface treating agent is particularly suitable for forming a coating on an optical member such as a lens and a filter (antireflective filter) to form a coating film that imparts antireflection and antifouling properties thereto. The antireflection filter includes an inorganic antireflection layer including a surface layer in the form of a silicon dioxide-based inorganic layer and an antifouling coating film formed on the surface layer.

Hereinafter, the present invention will be described in detail through synthesis examples for preparing perfluoropolyether-modified polyalkylether silane and examples for preparing a surface treatment agent. The present invention is not limited by the above synthesis examples and examples.

Synthetic example

The polyfluoropolyether 160g having a polyethylene oxide and an allyl ether functional group at both ends thereof, represented by the following Chemical Formula 5, 80 g of m-xylene hexafluoride, 0.1 g of chriroplatinic acid catalyst, and 15 g of trimethoxysilane are uniformly After mixing, the mixture was stirred for about 8 hours at a temperature of about 70 ℃. Thereafter, the solvent was distilled off to obtain 170 g of a perfluoropolyether-modified polyalkylethersilane represented by the following Chemical Formula 6 as a colorless transparent liquid.

Rf- [CH ₂ O- (C ₂ H ₄ O) n-CH ₂ CHCH ₂ ] ₂ ____________

Rf- [CH ₂ O- (C ₂ H ₄ O) nC ₃ H ₆ -Si- (OCH ₃ ) ₃ ] ₂ ____________ [Formula 6]

In Formula 5 and Rf 6 is _{-CF 2 O- (C 2 F 4} O) p - (CF 2 O) q -CF 2 - , and satisfy p / q ≒ 0.2 ~ 2, and p + q ≒ 40 Satisfies ˜180, and n is 1-5.

Comparative Synthesis Example

It is represented by the following formula (7) and uniformly the polyfluoropolyether 160g, m-xylene hexafluoride 80g, 0.1g chriroplatinic acid catalyst, 15g trimethoxysilane 15g with polyethylene oxide and allyl ether functional groups at both ends. After mixing, the mixture was stirred for about 8 hours at a temperature of about 70 ℃. Thereafter, the solvent was distilled off to obtain 165 g of a perfluoropolyether-modified silane represented by Chemical Formula 8, which was a colorless transparent liquid.

Rf- [CH ₂ O-CH ₂ CHCH ₂ ] ₂ ____________

Rf- [CH ₂ OC ₃ H ₆ -Si- (OCH ₃ ) ₃ ] ₂ ____________

In Formula 7, 8 and Rf is _{-CF 2 O- (C 2 F 4} O) p - (CF 2 O) q -CF 2 - , and satisfy p / q ≒ 0.2 ~ 2, and p + q ≒ 40 Satisfies ~ 180

Example 1

The perfluoropolyether-modified polyalkylethersilane obtained in the synthesis example was dissolved in perfluoro (2-butyltetrahydrofuran) at 20% by weight to prepare a surface treatment agent (antifouling coating liquid). Thereafter, 0.5 g of the surface treating agent was provided in a tablet (weight; 2.0 g) manufactured using steel wool, and a solvent was evaporated to prepare a tablet for vacuum deposition including perfluoropolyether-modified polyalkylethersilane. . Subsequently, a first antifouling film was formed on a substrate (substrate in which silicon dioxide and titanium dioxide were alternately vacuum deposited on an acrylic plate) in which an antireflection layer was formed in a vacuum deposition machine to which a tablet was applied. At this time, the inside of the vacuum evaporator is maintained at a pressure of about 5 × 10 ^-5 torr, the tablet is heated to about 400 ℃ on the molybdenum boat to evaporate the compound of formula (2).

Comparative Example 1

A second antifouling film was obtained in the same manner as in Example 1, except that the perfluoropolyether-modified in the Comparative Synthesis Example instead of the perfluoropolyether-modified polyalkylethersilane obtained in Synthesis Example 1. Silane was used.

Example 2

The perfluoropolyether-modified polyalkylether silane of the formula (6) obtained in the synthesis example was diluted in methyl perfluorobutyl ether in a 0.001 weight ratio to prepare a surface treatment agent (antifouling coating liquid). Subsequently, after impregnating the substrate (the substrate on which the acrylic plate was vacuum-deposited with silicon dioxide and titanium dioxide alternately) with the antireflection layer by using the inorganic material, the surface treatment agent was taken out one minute later and heated at 70 ° C. for 10 minutes. An antifouling film was formed.

Comparative Example 2

A fourth antifouling film was formed in the same manner as in Example 2, except that the perfluoropolyether-modified silane of Formula 8 obtained in Comparative Synthesis Example was used instead of the compound of Synthesis Example.

The physical properties of the antifouling films obtained in Examples 1 and 2 and Comparative Examples 1 and 2 were evaluated in the following manner. The physical property test of the antifouling films was carried out five times and the mode value was recorded. The results obtained are summarized in Table 1 below.

(a) Adhesiveness of the oil pen: A 3 centimeter line was drawn on the surface of the sample on which the antifouling film was formed using a Monamisa oil pen (MONAMI, oil magic ink), and its ease of sticking or surface wettability was visually determined. The criteria for evaluation are as follows.

(Circle): The handwriting consists of the points of a design, and it is a line.

(Triangle | delta): The handwriting is a point which is spherical but is several lines, and is seen by a wide line.

×: The handwriting is a broad line.

(b) Wipeability of the oil pen: The wire by the oil pen attached to the surface of the sample on which the antifouling film was formed was wiped with a small force using kimwipes® (kimberly-clark), and the ease of dropping was visually determined. The criteria for evaluation are as follows.

(Circle): The thing which can wipe a handwriting completely.

△: handwriting is cloudy.

X: The thing which cannot wipe a handwriting.

(c) Abrasion resistance: The surface of the sample on which the antifouling film was formed was applied to 500 grams of iron balls with fine wrinkled paper tape (3M, Tartan® Paper Tape # 200), and then rubbed 30 times, 50 times, and 70 times. , (b) was performed.

Here, in the case of performing abrasion while applying a load by using a paper tape, in a comparative experiment, abrasion occurs when frictional force is applied to the coating film, or the adhesion is damaged in some places, and then peeled off. In this case, the lower layer is exposed and the pigment and dye components of the oil pen are impregnated or adsorbed to the inorganic layer of the antireflective coating. Therefore, the wiping property of the oil pen at this time is significantly reduced.

TABLE 1

As shown in the results disclosed in Table 1, when the coating film is formed using the compound of Chemical Formula 6, it can be confirmed that the wiping property of the oil pen remains relatively long after some wear progresses and the adhesion of the oil pen decreases. there was. On the other hand, when the coating film is formed using the compound of Formula 8, it can be seen that the wiping property of the oil pen is easily degraded. This means that the compound of formula 6 has relatively little damage to adhesion as wear progresses.

As described above, the novel surface treatment compound represented by Chemical Formula 1 of the present invention is useful for forming an antifouling coating film having low surface energy and minimized adhesion to contaminants and excellent durability. Therefore, the antifouling coating film containing the new surface treatment compound as a main component can maintain the antifouling effect against contaminants in the long term, and it is easy to wipe off the contaminants even when the contaminants are attached and deteriorate function by rubbing. Or damage to its surface can be minimized.

Claims (9)

A perfluoropolyether-modified polyalkylether silane represented by the following formula (1), a surface treatment compound comprising a partial hydrolysis condensation product of the perfluoropolyether-modified polyalkylether silane or a mixture thereof . Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂ __________ [Formula 1] -CF ₂ O- (C ₂ F ₄ O) _p- (CF ₂ O) _q -CF ₂ -__________ -C ₂ F ₄ O- (C ₃ F ₆ O) _r- (CF ₂ O) _s -C ₂ F ₄ - _{_} _________ -C ₂ F ₄ O- (C ₃ F ₆ O) _t -C ₂ F ₄ -_________________ (In Formula 1, Rf is a linear or branched perfluoropolyether group having a bivalent terminal which is not an oxygen atom, and includes perfluoropolyether having 1 to 4 carbon atoms as a repeating unit, and has a number of 800 to 9000. The average molecular weight is satisfied and is represented by Formula 2, 3, or 4. In Formulas 2, 3, and 4, p, q, r, s, and t are integers of 1 to 80, respectively, wherein m is 1 to 3. N is an integer of 1 to 5, wherein a is an integer of 1 to 3, R is a lower alkyl or phenyl group having 1 to 4 carbon atoms, and X is a hydrolysis reactor having 1 to 3 carbon atoms. Oxyalkyl or acetoxy group, wherein the perfluoropolyether-modified polyalkylether silane is a perfluoropolyether-modified poly oxyalkylene silane.) delete delete Providing a surface treating agent for forming a coating film comprising a surface treating compound and a solvent; And Forming a coating film comprising the surface treatment compound on the surface of the object to be treated, The surface treatment compound may include a perfluoropolyether-modified polyalkylether silane represented by Formula 1, a partial hydrolysis condensation product of the perfluoropolyether-modified polyalkylether silane, or a mixture thereof. Coating film forming method. Rf- [CH ₂ O- (C _m H _2m O) _n -C ₃ H ₆ -Si (R) _3-a X _a ] ₂ __________ [Formula 1] -CF ₂ O- (C ₂ F ₄ O) _p- (CF ₂ O) _q -CF ₂ -__________ -C ₂ F ₄ O- (C ₃ F ₆ O) _r- (CF ₂ O) _s -C ₂ F ₄ - _{_} _________ -C ₂ F ₄ O- (C ₃ F ₆ O) _t -C ₂ F ₄ -_________________ (In Formula 1, Rf is a linear or branched perfluoropolyether group having a bivalent terminal which is not an oxygen atom, and includes perfluoropolyether having 1 to 4 carbon atoms as a repeating unit, and has a number of 800 to 9000. The average molecular weight is satisfied and is represented by Formula 2, 3, or 4. In Formulas 2, 3, and 4, p, q, r, s, and t are integers of 1 to 80, respectively, wherein m is 1 to 3. N is an integer of 1 to 5, wherein a is an integer of 1 to 3, R is a lower alkyl or phenyl group having 1 to 4 carbon atoms, and X is a hydrolysis reactor having 1 to 3 carbon atoms. Oxyalkyl or acetoxy group, wherein the perfluoropolyether-modified polyalkylether silane is a perfluoropolyether-modified poly oxyalkylene silane.) The method of claim 4, wherein the coating film comprises: heating the tablet impregnated with the surface treating agent to evaporate the surface treating compound; And And depositing the evaporated surface treatment compound on the surface of the object to be treated to form the coating film. The method of claim 5, wherein the surface treating agent has a composition including 10 to 70 wt% of the surface treating compound and an extra solvent. The method of claim 4, wherein the coating layer comprises: wet coating the surface treating agent on a surface of the object to be treated; And The coating film forming method, characterized in that formed by performing the step of drying the surface treatment agent. The method of claim 7, wherein the surface treating agent has a composition comprising 0.001 to 5 wt% of the surface treating compound and an extra solvent. The method of claim 7, wherein the object to be treated is an antireflection layer applied to an optical product, and the coating layer is an antifouling layer.