KR101843053B1 - Anti-fog composition with short perfluoroalkyl chains - Google Patents

Abstract

The present invention relates to an anti-fogging composition containing a short fluorinated alkyl group, specifically two short fluorinated alkyl groups having 6 or less carbon atoms in a single molecule. According to the resent invention, the anti-fogging composition containing the short fluorinated alkyl groups is more environmentally friendly and excellent in antifogging ability than existing anti-fogging compositions containing long alkyl fluorinated groups whose use is restricted due to environmental or harmful issues. In addition, the anti-fogging composition can be useful as anti-fogging agents for glasses, automobiles, helmets, goggles, and households.

Description

(Anti-fog composition with short perfluoroalkyl chains)

The present invention relates to a composition for preventing fogging containing a short fluorinated alkyl group, specifically two fluorinated alkyl groups having 6 or fewer carbon atoms in a molecule.

Products such as automobiles, glasses, goggles, toilet mirrors, etc. are necessary for daily life, but the use of the product may become uncomfortable depending on the temperature and environment. Steaming occurs mainly when the temperature inside and outside is different. It is this principle that when the cold water is poured into the cup and it is placed at room temperature, water droplets are formed on the outside of the cup and the hot water is poured into the cup.

In addition to the inconvenience that it is not easy to get a clear view of the driver when the steaming air is frozen, the motorcycle driver wearing a car or a helmet, or a pedestrian wearing glasses, And it is in a dangerous situation, so anti-fogging agent is very essential.

Patent Document 1 discloses an anti-fogging agent including a surfactant, an organic acid, a metal ion-containing agent, and the like. In addition, Patent Document 2 reports that a copolymer resin can be prepared by polymerizing a hydrophilic monomer, a hydrophobic monomer or the like to be used for preventing fogging. In Patent Document 3, various anti-fogging agents have been prepared using various surfactants.

Conventionally, fluorinated surfactants used in anti-fogging agents generally have fluorinated alkyl groups of 8 or more in length. Typical fluorinated compounds include perfluoroctanoic acid (PFOA) or perfluoroctanesulfonic acid (PFOS), which are perfluorinated compounds having eight carbons.

However, recently, it has been reported that PFOA or PFOS accumulates in human blood, and it is known that carcinogens can be detected in an animal experiment and can cause pregnancy disorder, etc. Therefore, it is classified as a dangerous substance, Of the total. The Risk Assessment Committee (RAC), supported by Germany and Norway, agrees to limit the use, manufacture and sale of PFOA-related substances and salts and products and mixtures containing them. . PFOA is a immortality of the biodegradable material should not toxic substances that accumulate in the body: it is known as (p ersistent, b io-accumulative , and t oxic substance PBT).

As described above, PFOA or PFOS has excellent performance, but its use is restricted due to environmental or harmful problems. Therefore, it is necessary to develop a fluorine compound that can replace the PFOA or PFOS.

Accordingly, the present inventors have made efforts to develop anti-fogging agents that can replace them, and have found that when a composition containing a compound containing two short fluorinated alkyl groups having 6 or less carbon atoms in one molecule is used as the anti-fogging alkyl group The present invention is more environmentally friendly than the anti-fogging composition containing the conventional long-fluoroalkyl group, which is limited in its use due to environmental or harmful problems, and is excellent in anti-fogging ability, so that it can be used for spectacles, automobiles, helmets, goggles, And thus the present invention has been completed.

Korean Patent Publication No. 10-2005-0036340 Korean Patent Publication No. 10-2008-0044140 Korean Patent Publication No. 10-2000-0007860

An object of the present invention is to provide a fluoroacrylate-based polymer.

It is another object of the present invention to provide a method for producing the fluoroacrylate-based polymer.

It is still another object of the present invention to provide a composition for preventing fogging which comprises the fluorine acrylate-based polymer.

Another object of the present invention is to provide a fogging prevention method.

In order to achieve the above object,

The present invention provides a fluoroacrylate-based polymer represented by the following Formula 1:

[Chemical Formula 1]

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ^a , R ^b , R ^c , R ^d , M and n are as defined in the description of the invention).

Further, according to the present invention,

A fluorine-based acrylate represented by the following formula (2); Acrylic acid represented by the following general formula (3); Polyethylene glycol acrylate represented by the following formula (4); And a step of polymerizing the alkyl acrylate represented by the following formula (5) in the presence of an initiator to prepare a fluoroacrylate-based polymer represented by the above formula (1).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

(In the above formulas 2 to 5,

R ¹ , R ² , R ³ , R ⁴ , R ^a , R ^b , R ^c , R ^d , M and n are as defined in the description of the invention.

Further, the present invention provides a composition for preventing fogging comprising the fluoroacrylate-based polymer represented by Formula 1 above.

Further, the present invention provides a fogging prevention method comprising adhering the anti-fogging composition to a subject to be treated.

The anti-fogging composition containing two fluorinated alkyl groups of not more than 6 carbon atoms in the molecule according to the present invention is more environmentally friendly than the anti-fogging composition containing the conventional long fluoroalkyl group whose use is restricted due to environmental or harmful problems Can be effectively used as an anti-fogging agent for spectacles, automobiles, helmets, goggles and households.

Figs. 1 to 4 are images obtained by spraying hot water vapor on a glass plate coated with the composition for preventing fogging according to Examples and Comparative Examples,

Hereinafter, the present invention will be described in detail.

The present invention provides a fluoroacrylate-based polymer represented by the following formula (1):

[Chemical Formula 1]

(In the formula 1,

R ¹ and R ² are each independently - (CH ₂ ) x- (CF ₂ ) y-CF ₃ , wherein x is 1 or 2 and y is 1 to 5;

R ³ is straight or branched C ₁₂ -C ₃₀ alkyl; Or straight or branched C ₁₂ -C ₃₀ alkenyl having at least one double bond;

R ^a , R ^b , R ^c and R ^d are each independently hydrogen or methyl;

M is an alkali metal cation, an alkaline earth metal cation or NH ₄ ⁺ ;

n is an integer from 4 to 10; And

The molar ratio of a: b: c: d is 1: 5.5 - 6.5: 0.6 - 1.2: 0.5 - 1.0.

Hereinafter, the fluoroacrylate-based polymer represented by Formula 1 according to the present invention will be described in detail.

Preferably,

Wherein R ¹ and R ² are each independently - (CH ₂ ) x- (CF ₂ ) y-CF ₃ , wherein x is 1 or 2 and y is 1 to 3;

R ³ is linear or branched C ₁₂ -C ₂₀ alkyl;

R ^a is methyl, R ^b is hydrogen, R ^c is methyl, R ^{d is} hydrogen;

M is an alkali metal cation;

n is 4 to 10; And

The molar ratio of a: b: c: d is 1: 5.5 - 6.5: 0.6 - 1.2: 0.5 - 1.0.

More preferably,

Wherein R ¹ and R ² are -CH ₂ CF ₂ CF ₃ ,

R ³ is linear or branched C ₁₂ -C ₁₈ alkyl,

R ^a is methyl, R ^b is hydrogen, R ^c Is methyl, R &^lt; ^d > is hydrogen,

M is an alkali metal cation,

n is from 4 to 8; And

The molar ratio of a: b: c: d is 1: 5.8 - 6.0: 0.8 - 0.9: 0.6 - 0.7.

The fluoroacrylate-based polymer represented by Formula 1 according to the present invention is not particularly limited as long as the fluorinated alkyl group has 6 or less carbon atoms, but R ¹ and R ² are each independently - (CH ₂ ) x- (CF ₂ ) y-CF ₃ , wherein x is 1 or 2, y is preferably 1 to 3, and is preferably -CH ₂ CH ₂ CF ₂ CF ₃ or -CH ₂ CH ₂ CF ₂ CF ₂ CF ₃ And most preferably -CH ₂ CF ₂ CF ₃ .

When the number of carbon atoms in the fluorinated alkyl group is less than 1, an acrylate-based polymer showing the effect of preventing fogging can not be obtained. When the number of carbon atoms in the fluorinated alkyl group exceeds 6, the number of fluorine atoms may be detrimental to the human body and the environment The present invention is intended to solve the problem of the present invention.

The fluoroacrylate polymer according to the present invention preferably has a weight average molecular weight ranging from 500,000 to 2,000,000, more preferably from 800,000 to 1,500,000, but is not limited thereto.

The present invention also provides a fluorinated acrylate represented by the following general formula (2): Acrylic acid represented by the following general formula (3); Polyethylene glycol acrylate represented by the following formula (4); And a step of polymerizing the alkyl acrylate represented by the following formula (5) in the presence of an initiator to prepare a fluoroacrylate-based polymer represented by the above formula (1).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

(In the above formulas 2 to 5,

R ¹ , R ² , R ³ , R ⁴ , R ^a , R ^b , R ^c , R ^d , M and n are as defined in Formula 1.

Hereinafter, a method for producing a fluoroacrylate-based polymer according to the present invention will be described in detail.

In the process for producing the fluoroacrylate-based polymer represented by the formula (1) according to the present invention, it can be used without particular limitation, as long as it is a reaction condition for usually polymerizing acrylate. Examples of the initiator include benzoyl peroxide, azobisisobutyronitrile, di-t-butyl peroxide, lauryl peroxide, cumene hydroperoxide, t-butyl peroxypivalate, diisopropyl peroxide Carbonate and the like can be used. The polymerization initiator may be used in an amount of 0.01 to 20 parts by weight, for example, 0.01 to 10 parts by weight, based on 100 parts by weight of the total of the monomers of the formulas (2) to (5).

The solvent is inert to the monomers of the formulas (2) to (5) and can be used without particular limitation as long as it dissolves the monomers. Examples of the solvent include toluene, xylene, chloroform, isopropyl alcohol, pentane, hexane, heptane, , Benzene, petroleum ether, tetrahydrofuran, 1,4-dioxane, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, 1,1,2,2-tetrachloroethane, Trichloroethane, trichlorethylene, perchlorethylene, tetrachlorodifluoroethane, trichlorotrifluoroethane, and the like. The solvent may be used in an amount of 50 to 2000 parts by weight, for example, 50 to 1000 parts by weight, based on 100 parts by weight of the total of the monomers of formulas (2) to (5).

The fluorine-containing acrylate represented by the general formula (2) contains two fluorinated alkyl groups in one molecule in order to solve the problem of being harmful to the human body and the environment as the number of carbon atoms in the fluorinated alkyl group increases, As the fluorinated alkyl group containing less than 6 carbon atoms, a monomer serving as an effect of preventing fogging can be produced as follows.

First, a step (step 1) of producing 1,3-di-fluorinated alkoxy-2-propanol under the condition that the amount of epichlorohydrin: fluorinated alcohol: base is about 1: 0.9 to 2.5: 0.8 to 2.6 molar ratio, (Step 2) of producing a fluorinated acrylate compound represented by the general formula (2) under catalytic conditions in an amount of 1: 1.1 to 2.5 mol of 1,3-dihydrofluorinated alkoxy-2-propanol and methacrylic acid or acrylic acid, . ≪ / RTI >

Specifically, the fluorinated alcohol in Step 1 is CF ₃ CF ₂ CH ₂ -OH, CF ₃ CF ₂ CF ₂ CH ₂ -OH, CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ -OH, CF ₃ CF ₂ CF ₂ CF CH ₂ CH ₂ CF ₃ having ₂ molecular formula, such as -OH - may be a _{(CF 2) y- (CH 2} ) x-OH is an alcohol, and where x is 1 or 2, y is a number from 1 to 5 Preferably, x is 1 and y can be 3.

In addition, the base of step 1 is an alkali metal compound, which is an alkali metal hydroxide, preferably potassium hydroxide or sodium hydroxide, more preferably sodium hydroxide. The base may be a solid base.

Further, as the solvent of the step 1, a general nonpolar solvent such as hexane, toluene, xylene, chloroform and the like can be used, and toluene can be preferably used.

The catalyst of step 2 may be a conventional acid catalyst, preferably p-toluenesulfonic acid having excellent reactivity.

 In addition, the step 2 may further include a polymerization inhibitor, and examples thereof include hydroquinone, hydroquinone monoester, benzoquinone, and combinations thereof. Most preferably, it may be hydroquinone.

Further, as the solvent of the step 2, a general nonpolar solvent such as hexane, toluene, xylene, chloroform and the like can be used, and toluene can be preferably used.

The acrylic acid represented by the general formula (3) may be replaced with maleic anhydride as a monomer added to increase solubility in water.

The polyethylene glycol methacrylate represented by the general formula (4) preferably has an average molecular weight of 400 to 1000, more preferably an average molecular weight of 500 to 600.

The alkyl acrylate represented by the general formula (5) is a straight chain or branched alkyl having 10 to 20 carbon atoms or a straight chain or branched chain alkenyl having at least one double bond, preferably having 12 to 18 carbon atoms, Straight chain alkyl having 18 carbon atoms.

Further, the present invention provides a composition for preventing fogging comprising the fluoroacrylate-based polymer represented by Formula 1 above.

Specifically, in the anti-fogging composition of the present invention, the fluoroacrylate-based polymer represented by Formula 1 may be contained in an amount of 1 to 5% by weight based on the total weight of the anti-fogging composition. The anti-fogging composition according to the present invention can prevent the fogging by penetrating and adhering to the glass surface in the optimum range, and by strengthening the bonding force of the composition against the glass surface, the anti-fogging action is remarkably sustained, have. If the amount of the fluoroacrylate-based polymer represented by the formula (1) is less than 1% by weight, the effect of preventing fogging may deteriorate due to insufficient dispersion capability. If the fluoroacrylate-based polymer is contained in an amount exceeding 5% by weight, , It is preferably 1 to 5% by weight from the standpoint of performance and economics.

In this case, the concentration of the fluoroacrylate-based polymer represented by Formula 1 may be 0.01 to 50 wt%.

The anti-fogging composition according to the present invention is preferably in the form of a solution, an emulsion or an aerosol, and is preferably selected from the group consisting of polyvinyl alcohol, polyvinyl pyrrolidone, sulfosuccinic ester salt, water, nonionic surfactant, anionic surfactant, , A solvent such as polyethylene glycol and an alcohol having 2 to 5 carbon atoms, and the like.

The polyvinyl alcohol preferably has a molecular weight of 31,000 to 51,000, and the polyvinyl pyrrolidone preferably has an average molecular weight of 360,000. In addition, the sulfosuccinic acid ester salt preferably has 6 to 12 carbon atoms in the alkyl group, Sodium, potassium and lithium are preferable, and sodium salt having 8 alkyl groups is more preferable.

Further, the composition for preventing fogging according to the present invention may further be added to the range of not hindering the effect of the fogging on the coloring matter or the fragrance used in ordinary fields.

As a result of measuring the anti-fogging properties of the anti-fogging composition according to the present invention, it can be confirmed that the anti-fogging properties in Examples 1, 2, 5, 6, 4 and 3 are excellent, Comparative Examples 3 and 4 containing no fluorine-based polymer exhibited almost no antifogging property, and were superior to Comparative Examples 1 and 2 which are conventional anti-fogging agents (see Experimental Example 1).

Therefore, the anti-fogging composition containing two fluorinated alkyl groups of 6 or less carbon atoms in the molecule according to the present invention is superior in anti-fogging composition containing a long fluorinated alkyl group which is limited in its use due to environmental or harmful problems It is environmentally friendly and has excellent anti-fogging ability, so it can be usefully used as an anti-fogging agent for eyeglasses, automobile, helmet, goggles, and home.

Further, the present invention provides a fogging prevention method comprising the step of adhering the anti-fogging composition to the object to be treated.

Specifically, the composition for preventing fogging according to the present invention can be applied to the object to be treated by a conventionally known method. Usually, the anti-fogging composition is dispersed in an organic solvent or water, diluted, and dried by adhering to the surface of the material to be treated by a known method such as dip coating, spray coating, or bubble coating. If necessary, insecticides, softeners, antibacterial agents, flame retardants, antistatic agents, paint fixing agents, anti-wrinkle agents and the like may be added and used in combination.

The object to be treated can be applied to an article requiring prevention of fogging such as a spectacle, a vehicle, a goggle, or a home.

Hereinafter, examples and experimental examples of the present invention will be described in detail.

However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the present invention is not limited to the following Examples and Experimental Examples.

< Manufacturing example  1> Fluorine Acrylate series  Polymer manufacturing 1

step 1: 1 (3-bis (2,2,3,3,3-pentafluoropropoxy) propan-2-yl methacrylate (F2-F2-MMA)

A 1 L three-necked flask equipped with a stirrer, a heater, a condenser and a thermometer was charged with 2.1 mol of alcohol CF ₃ CF ₂ CH ₂ -OH, 0.0625 mol of TBAB (tetrabutyl ammonium bromide) and 300 mL of toluene. 2 mol of NaOH was slowly added while stirring at room temperature and stirred for 30 minutes. 1 mol of epichlorohydrin was slowly added dropwise so that the internal temperature did not exceed 30 ° C, and the reaction was carried out at 80 to 100 ° C for about 24 hours with stirring. The reaction was traced by GC and the reaction was terminated when the raw material, epichlorohydrin, disappeared. After completion of the reaction, the mixture was washed three times with 100 ml of water each time, and the water layer was removed. The organic layer was dried with 10 g of anhydrous magnesium sulfate (MgSO4) to remove residual moisture. The toluene was completely removed by using an evaporator and then distilled under reduced pressure to obtain pure (CF ₃ CF ₂ CH ₂ OCH ₂ ) ₂ CH-OH. In a three-neck round flask, 400 mL of toluene, 1 mol of the above-prepared (CF ₃ CF ₂ CH ₂ OCH ₂ ) ₂ CH-OH, 2 mol of methacrylic acid, 0.2 mol of p-toluenesulfonic acid monohydrate and 0.0373 mol of hydroquinone , And water was removed using Dean Stark, and the mixture was stirred at 105 ° C. After the reaction was terminated by monitoring the reaction with GC, the remaining acrylic acid was neutralized with potassium carbonate. The mixture was poured into a separatory funnel and washed three times with 100 ml of water. The water layer was removed, and residual organic layer was dried with 10 g of anhydrous magnesium sulfate (MgSO ₄ ). Toluene was all removed using an evaporator and then subjected to vacuum distillation to obtain pure 1,3-bis (2,2,3,3,3-pentafluoropropoxy) propan-2-yl methacrylate.

Step 2: Fluorine Acrylate series  Manufacture of Polymers

To a 100-mL three-necked flask, 20 mL of toluene was added, and 1,3-bis (2,2,3,3,3-pentafluoropropoxy) propan-2-yl methacrylate 0.0046 mol, 2.86 g), monomers of acrylic acid (0.0396, 2.86 g), polyethylene glycol methyl ether methacrylate (molecular weight 500, 0.0057 mol, 2.86 g) and octadecyl acrylate (0.0044 mol, 1.43 g) A 15 mL solution and benzoyl peroxide (0.0248, 1.2 g) were slowly added dropwise and reacted overnight with stirring. After completion of the reaction, the toluene was distilled off under reduced pressure, and the reaction product was dissolved in water, neutralized with NaOH solution, and water was evaporated to prepare a fluoroacrylate polymer (weight average molecular weight mw: 800,000 - 1,500,000).

< Manufacturing example  2> Fluorine Acrylate series  Polymer manufacturing 2

A fluorine acrylate-based polymer was prepared in the same manner as in Preparation Example 1, except that polyethylene glycol methyl ether methacrylate (0.003 mol, 2.86 g) having a molecular weight of 950 was used instead of the molecular weight 500 in the step 2 of Preparation Example 1 .

< Manufacturing example  3> Fluorine Acrylate series  Polymer manufacturing 3

A fluorine acrylate-based polymer was prepared in the same manner as in Preparation Example 1, except that dodecyl acrylate (0.0059 mol, 1.43 g) was used instead of octadecyl acrylate in the step 2 of Preparation Example 1.

< Comparative Manufacturing Example  1> Fluorine Acrylate series  Polymer manufacturing

step 1: 3 , 3,4,4,5,5,6,6,7,7,8,8,8- Tridecafluorooctyl Methacrylate Manufacture

In a three-neck round flask, 400 mL of toluene, 1 mol of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol, 2 mol of methacrylic acid, 0.2 mol of sulfonic acid monohydrate and 0.0373 mol of hydroquinone were added thereto, and water was removed using a Deanstock, and the mixture was stirred at 105 ° C. After the reaction was terminated by monitoring the reaction with GC, the remaining acrylic acid was neutralized with potassium carbonate. The mixture was poured into a separatory funnel and washed three times with 100 ml of water. The water layer was removed, and residual organic layer was dried with 10 g of anhydrous magnesium sulfate (MgSO ₄ ). Toluene was all removed using an evaporator and then subjected to vacuum distillation to obtain pure 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl methacrylate .

Step 2: Fluorine Acrylate series  Manufacture of Polymers

(2,2,3,3,3-pentafluoropropoxy) propan-2-yl methacrylate was prepared in the same manner as Step 1 of Comparative Preparation Example 1 except that 1,3-bis (2,2,3,3,3-pentafluoropropoxy) Except that 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl methacrylate (0.0066 mol, 2.86 g) was used instead of 3,3,4,4,5,5,6,6,7,7,8,8,8- Fluoroacrylate polymer was prepared in the same manner as in (1).

< Example  1 to 6> Kim Se-rim  Preparation of a composition for prevention

To prepare anti-fogging compositions according to the present invention, the anti-fogging compositions of Examples 1 to 6 were prepared using the fluoroacrylic polymers prepared in Preparation Example 1 in the compositions shown in Table 1 below.

< Comparative Example  1> Kim Se-rim  Preparation of a composition for prevention

Comparative Example 1 was prepared in the same manner as commercially available anti-fogging agent (defogit of biofilm) except that 94 wt% of water, 5 wt% of a fluorine-based nonionic surfactant having 6, 8, and 10 fluorocarbon groups, and 6 wt% And 1% by weight of a water-soluble polymer.

< Comparative Example  2> Kim Se-rim  Preparation of a composition for prevention

The anti-fogging composition of Comparative Example 2 was prepared using the fluoroacrylic polymer prepared in Comparative Preparation Example 1 in the composition shown in Table 1 below.

< Comparative Example  3 to 5> Kim Se-rim  Preparation of a composition for prevention

Anti-fogging compositions of Comparative Examples 3 to 5 were prepared using the fluoroacrylic polymers prepared in Preparation Example 1 in the compositions shown in Table 1 below.

Fluorine
Polymer Fluorine
Nonion
Surfactants Polyvinyl
Alcohol Polyvinyl
Pyrrolidone Sulfosuccinic acid
Ester salt water Example 1 One 0 One 0 0 98 Example 2 5 0 One 0 0 94 Example 3 One 0 5 0 0 94 Example 4 One 0 One 0.5 0.5 97 Example 5 5 0 One 0.5 0.5 93 Example 6 2 0 2 One One 94 Comparative Example 1 One 5 One 0 0 94 Comparative Example 2 5 0 One 0.5 0.5 94 Comparative Example 3 0 0 One 0.5 0.5 98 Comparative Example 4 0 0 2 One One 96 Comparative Example 5 6 0 One 0 0 93

(However, the fluorinated polymer of Comparative Example 2 is a polymer of Comparative Preparation Example 1).

< Experimental Example  1> Kim Se-rim  Prevention test

Experiments were conducted as follows to test the antifogging properties of the antifogging compositions prepared in Examples 1 to 6 and Comparative Examples 1 to 5 according to the present invention.

Specifically, the same amount (0.02 g) of anti-fogging composition was applied to a cleaned glass plate for the anti-fogging test in the same area (9 cm ² ), then the hot steam was continuously applied, Respectively. The results are shown in Figs. 1 to 4 and Table 2.

Immediately 30 minutes later After 1 hour 1 hour and 30 minutes Example 1 ◎ ◎ ◎ ◎ Example 2 ◎ ◎ ◎ ◎ Example 3 ◎ ◎ △ Χ Example 4 ◎ ◎ ○ △ Example 5 ◎ ◎ ◎ ○ Example 6 ◎ ◎ ○ △ Comparative Example 1 ◎ ◎ ○ Χ Comparative Example 2 ◎ ◎ △ Χ Comparative Example 3 ◎ Χ Χ Χ Comparative Example 4 ◎ Χ Χ Χ Comparative Example 5 ◎ ◎ ◎ ◎

(In Table 2, &quot; Excellent &quot;, &quot; Excellent &quot;, &quot; Fair &quot;, &quot; Poor &

Figs. 1 to 4 are images obtained by spraying hot water vapor on a glass plate coated with the composition for preventing fogging according to Examples and Comparative Examples to observe the degree of fogging retention over time.

The anti-fogging composition according to the present invention shows excellent anti-fogging properties. Specifically, it can be confirmed that the anti-fogging properties in Examples 1, 2, 5, 6, 4 and 3 are excellent, and Comparative Examples 3 and 4, which do not contain the fluoropolymer according to the present invention, And it is superior to Comparative Examples 1 and 2 which are conventional anti-fogging agents.

Claims (10)

A fluoroacrylate-based polymer represented by the following formula (1)
[Chemical Formula 1]

(In the formula 1,
R ¹ and R ² are each independently - (CH ₂ ) x- (CF ₂ ) y-CF ₃ , wherein x is 1 or 2 and y is 1 to 5;
R ³ is straight or branched C ₁₂ -C ₃₀ alkyl; Or straight or branched C ₁₂ -C ₃₀ alkenyl having at least one double bond;
R ^a , R ^b , R ^c And R &lt; ^d &gt; are each independently hydrogen or methyl;
M is an alkali metal cation, an alkaline earth metal cation or NH ₄ ⁺ ;
n is an integer from 4 to 10; And
The molar ratio of a: b: c: d is 1: 5.5 - 6.5: 0.6 - 1.2: 0.5 - 1.0.
The method according to claim 1,
Wherein the fluoroacrylate-based polymer has a weight average molecular weight ranging from 500,000 to 2,000,000.
The method according to claim 1,
Wherein R ¹ and R ² are each independently - (CH ₂ ) x- (CF ₂ ) y-CF ₃ , wherein x is 1 or 2 and y is 1 to 3;
R ³ is linear or branched C ₁₂ -C ₂₀ alkyl;
R ^a is methyl, R ^b is hydrogen, R ^c Is methyl, R &lt; ^d &gt; is hydrogen;
M is an alkali metal cation;
n is 4 to 10; And
wherein the molar ratio of a: b: c: d is 1: 5.5 - 6.5: 0.6 - 1.2: 0.5 - 1.0.
A fluorine-based acrylate represented by the following formula (2); Acrylic acid represented by the following general formula (3); Polyethylene glycol acrylate represented by the following formula (4); And an alkyl acrylate represented by the following formula (5) in the presence of an initiator; And
The method of claim 1, wherein the fluorinated acrylate polymer is neutralized with NaOH after the polymerization.
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

(In the above formulas 2 to 5,
R ¹ , R ² , R ³ , R ⁴ , R ^a , R ^b , R ^c , R ^d and n are as defined in claim 1.
5. The method of claim 4,
The initiator may be selected from the group consisting of benzoyl peroxide, azobisisobutyronitrile, di-t-butyl peroxide, lauryl peroxide, cumene hydroperoxide, t-butyl peroxypivalate, diisopropyl peroxydicarbonate And at least one kind selected from the group consisting of:
A composition for preventing fogging comprising the fluoroacrylate-based polymer according to claim 1.
The method according to claim 6,
Wherein the fluoroacrylate-based polymer is contained in an amount of 1 to 5 wt% based on the total weight of the composition for preventing fogging.
The method according to claim 6,
The anti-fogging composition may further comprise at least one member selected from the group consisting of polyvinyl alcohol, polyvinyl pyrrolidone, sulfosuccinic acid ester salt, water, propylene glycol, polyethylene glycol and an alcohol having 2 to 5 carbon atoms By weight of the composition.
A method of preventing fogging comprising the step of adhering the anti-fogging composition of claim 6 to a subject to be treated.
10. The method of claim 9,
Wherein the object to be treated is a lens for a spectacle, a vehicle, a goggle, or a home.

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