KR100481122B1 - Fluorine-Containing Acrylates or Methacrylates, Crosslinker and Soft Lens Prepared by Using the Same - Google Patents

Abstract

The present invention relates to novel fluorine-containing acrylate or methacrylate monomers, polyacrylates or polymethacrylates and soft lenses prepared therefrom, more particularly the monomers of the present invention are represented by the formula:

, or

In the above formula, R is H or CH ₃ , R 'is (CH ₂ ) _b -Rf- (CH ₂ ) _c -OH, b and c are integers of 1-4, Rf is substituted or not Ring fluoro alkyl, fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl.

Description

Fluorine-Containing Acrylates or Methacrylates, Crosslinker and Soft Lens Prepared by Using the Same}

The present invention relates to novel fluorine-containing acrylate or methacrylate monomers and crosslinking agents, and more particularly to novel fluorine-containing acrylate or methacrylate monomers, polyacrylates or polymethacrylates prepared therefrom. And a soft lens.

Generally, contact lenses are divided into hard lenses based on methacrylate (MA) and soft lenses based on 2-hydroxyethyl methacrylate (HEMA). The use of soft lenses with relatively good general lens characteristics such as oxygen permeability and water content is expanding. This is because HEMA, unlike MA, has a hydroxy group, which is a representative hydrophilic molecular structure in the monomer, and has a high water content (Refojo et al., J. Appl. Poly. Sci. , 9: 2425 (1965)).

On the other hand, hydrogel refers to a cross-linked polymer containing a large amount of water in the equilibrium state, a material having a large number of biomedical applications such as contact lenses, medical polymers (see US Patent No. 4300820). Currently, hydrogels used in lenses are mostly produced by radical thermal polymerization reaction after 2-hydroxyethyl methacrylate is used as a monomer and mixed with a small amount of crosslinking agent. However, a lens made of such a material has a limited water content due to its material property, and there is a limitation in wearing comfort, and a problem such as protein adhesion occurs for a long time (Wilson et al., Encyclo. Of Chem. Tech). ., 7: 192 (1976); and U.S. Patent No. 6,096,138).

As the wearability of the lens is known to be closely related to the moisture content, various developments have been attempted to increase the moisture content, and some have been commercialized, and commercially available lenses have a high absorption rate of N-vinyl pyrrolidone or polyvinyl alcohol. It is prepared using as a monomer (co-monomer). However, lenses using such monomers have poor mechanical strength and are mainly used for disposable lenses only and are not suitable for long-term use (Refojo. Et al., Cont. & Intracular Lens Med. J. , 1:36 (1975)).

On the other hand, fluorine-containing resins are not only used in optical communication devices and semiconductor insulating films because of their low refractive index, but also in contact lenses because of their high moisture content and protein-adhesion inhibitory effect. Only in areas of concern (Scheirs et al., Trends in Poly. Sci. , 3: 74 (1995). In addition, silicone-containing resins are used mainly for hard lenses due to their excellent oxygen permeability, but in general, silicone-based resins are hydrophobic and thus have limited water content for hydrogel-type lenses. Although some monomers containing both fluorine and silicon have been developed, they are difficult to commercialize due to high manufacturing costs (US Patent No. 5945498).

Throughout this specification many patent documents and articles are referenced and their citations are indicated. The disclosures of cited patent documents and articles are incorporated herein by reference in their entirety, so that the level of the technical field to which the present invention belongs and the contents of the present invention are more clearly explained.

It is therefore an object of the present invention to provide novel fluorine-containing acrylate or methacrylate monomers.

Another object of the present invention is to provide a novel fluorine-containing diacrylate or dimethacrylate crosslinking agent.

Another object of the present invention is to provide a novel fluorine-containing polyacrylate or polymethacrylate.

Another object of the present invention is to provide a method for producing a novel fluorine-containing polyacrylate or polymethacrylate.

Another object of the present invention is to provide a hydrogel soft lens comprising the fluorine-containing polyacrylate or polymethacrylate of the present invention.

According to one aspect of the present invention, the present invention provides a fluorine-containing acrylate or methacrylate monomer represented by Formula 1 below:

In the above formula, R is H or CH ₃ , R 'is (CH ₂ ) _b -Rf- (CH ₂ ) _c -OH, b and c are integers of 1-4, Rf is substituted or not Ring fluoro alkyl, fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl.

According to another aspect of the present invention, the present invention provides a fluorine-containing acrylate or methacrylate monomer represented by the following general formula (2):

Wherein R is H or CH ₃ , R 'is (CH ₂ ) _b -Rf- (CH ₂ ) _c -OH, and Rf is substituted or unsubstituted fluoroalkyl, fluorocycloalkyl, Fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl, wherein b and c are integers of 1-4.

According to another aspect of the present invention, the present invention provides a fluorine-containing acrylate or methacrylate monomer represented by the following general formula (3):

In the above formula, R is H or CH ₃ and R 'is CH ₂ -CF ₂ -CF ₂ -CF ₂ -CF ₂ -CH ₃ .

In order to maximize the water content of the conventional hydrogel-type soft lens, the inventors have developed the monomers of Chemical Formulas 1 to 3 in which a high water content fluorine atom and a hydroxyl group, which is a representative hydrophilic group, are simultaneously introduced.

In the monomer of the present invention, Rf is substituted or unsubstituted C ₁ -C ₁₈ fluoro alkyl, C ₁ -C ₁₈ fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or Fluoro alkaryl; And a is preferably an integer of 1-4.

According to a more preferred embodiment of the monomers of the invention, the fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl comprises 1-24 fluorine atoms.

According to another modification of the present invention, Rf is represented by the following Chemical Formula 4:

CF ₂ O (CF ₂ CF ₂ O) _d

In the above formula, d is an integer of 1-100, preferably an integer of 1-10.

In order to form a hydrogel using the monomer of this invention, it is preferable to use a small amount of crosslinking agents.

Accordingly, according to another aspect of the present invention, the present invention provides a fluorine-containing diacrylate or dimethacrylate crosslinker represented by the following formula (5):

Wherein R is H or CH ₃ , Rff is substituted or unsubstituted fluoro alkyl, fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl, And a is an integer of 1-10.

In a preferred crosslinking agent of the invention, Rff is substituted or unsubstituted C ₁ -C ₃₆ fluoro alkyl, C ₁ -C ₃₆ fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl Or fluoro alkaryl; And a is an integer of 1-4.

According to a preferred embodiment of the present invention, the fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl includes 1-24 fluorine atoms.

According to another variant of the invention, Rff is represented by the following formula (4):

[Formula 4]

CF ₂ O (CF ₂ CF ₂ O) _d

In the above formula, d is an integer of 1-100, preferably an integer of 1-10.

The crosslinking agent of the present invention described above is specially manufactured by the present inventors according to the purpose of maximizing the moisture content.

In addition, when forming a hydrogel using the monomer of this invention, in addition to the crosslinking agent mentioned above, ethylene glycol dimethacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, diethylene glycol dimethacrylate, tri Conventionally used crosslinking agents such as ethylene glycol dimethacrylate or tetraethylene glycol dimethacrylate may be used.

A polymer is formed using the monomer and crosslinking agent mentioned above.

Accordingly, according to another aspect of the present invention, the present invention provides a fluorine-containing polyacrylate or polymethacrylate having the following formula (6) as a repeating unit:

In the above formula, R is H or CH ₃ , R 'is (CH ₂ ) _b -Rf- (CH ₂ ) _c -OH, b and c are integers of 1-4, Rf is substituted or not Ring fluoro alkyl, fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl, n is an integer from 1-1,000.

According to another aspect of the present invention, the present invention provides a fluorine-containing polyacrylate or polymethacrylate having the following general formula (7):

In the above formula, R is H or CH ₃ , R 'is (CH ₂ ) _b -Rf- (CH ₂ ) _c -OH, b and c are integers of 1-4, Rf is substituted or not Ring fluoro alkyl, fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl, n is an integer from 1-1,000.

According to another aspect of the present invention, the present invention provides a fluorine-containing polyacrylate or polymethacrylate having the following formula 8 as a repeating unit:

In the above formula, R is H or CH ₃ , R 'is (CH ₂ ) _b -Rf- (CH ₂ ) _c -OH, b and c are integers of 1-4, Rf is substituted or not Ring fluoro alkyl, fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl, n is an integer from 1-1,000.

In a preferred polymer of the invention, Rf is substituted or unsubstituted C ₁ -C ₁₈ fluoro alkyl, C ₁ -C ₁₈ fluoro cycloalkyl, fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl Or fluoro alkaryl; And a is an integer of 1-4.

In a more preferred polymer of the present invention, the fluoro aryl, fluoro arylalkyl, fluoro heteroarylalkyl or fluoro alkaryl contains 1-24 fluorine atoms.

According to another modification of the present invention, Rf is represented by the following Chemical Formula 4:

[Formula 4]

CF ₂ O (CF ₂ CF ₂ O) _d

In the above formula, d is an integer of 1-100, preferably an integer of 1-10.

According to a preferred embodiment of the invention, said n value representing the degree of polymerization is an integer of 1-1,000, preferably an integer of 50-500.

According to another aspect of the present invention, the present invention provides a mixed solution comprising (a) a fluorine-containing monomer component corresponding to any one of Formulas 1 to 3, a fluorine-containing crosslinking agent of Formula 5, and a radical initiator Preparing; And (b) provides a method of producing a fluorine-containing polyacrylate or polymethacrylate comprising the step of inducing a thermal polymerization reaction by supplying heat to the mixed solution.

In the production method using the fluorine-containing monomer component corresponding to any one of the formulas (1) to (3), preferably the mixed solution is acrylic acid, methacrylic acid, acrylamide, N, N-dimethylacrylamide, methacrylamide, Group consisting of methyl methacrylate, 2-hydroxyethylmethacrylate, glyceryl methacrylate, N-vinyl-2-pyrrolidone, α-methylene-N-methyl-pyrrolidone and 1-vinyl imidazole It further comprises a hydrophilic monomer component selected from. In the production method of the present invention, in the case of using only the fluorine-containing monomer of the present invention corresponding to any one of the formulas (1) to (3), water content and oxygen permeability is better than when used with the hydrophilic monomer component described above, When the quality of the lens may be slightly deteriorated, such as a lens or an entry type lens, the hydrophilic monomer component is used in consideration of the cost of obtaining the monomer component.

As such, when both the fluorine-containing monomer and the conventional hydrophilic monomer of the present invention are used, the weight ratio of the fluorine-containing monomer: hydrophilic monomer is preferably 95: 5-10: 90, more preferably 95: 5- 50:50.

According to a preferred embodiment of the preparation method of the present invention, the radical initiator is azo bisisobutyronitrile, 2,2'- azo bis (2,4-dimethylpentanenitrile), 2,2'- azo bis (2 , 4-dimethylvaleronitrile), benzoyl peroxide, di (secbutyl) peroxydicarbonate and isopropylperoxydicarbonate, and the like.

According to a preferred embodiment of the present invention, the mixed solution comprises 0.5-20 parts by weight of the crosslinking agent and 0.01-10 parts by weight of the initiator with respect to 100 parts by weight of the monomer component, more preferably the mixed solution comprises the monomer component. 1-3 parts by weight of the crosslinking agent and 0.1-5 parts by weight of the initiator based on 100 parts by weight.

In the production method of the present invention, the polymerization reaction is carried out by a thermal polymerization method. The polymerization temperature and time vary depending on the type and amount of monomers used, the type and amount of initiator, etc., and are usually 10-60 minutes at 90-150 ° C., preferably 20-40 minutes at 90-120 ° C. .

The fluorine-containing polyacrylates or polymethacrylates of the present invention described above are preferably used in soft lenses in the form of hydrogels.

Therefore, according to another aspect of the present invention, the present invention provides a hydrogel soft lens comprising fluorine-containing polyacrylate or polymethacrylate having the formula 6, 7 or 8 as a repeating unit.

According to another aspect of the present invention, the present invention provides a hydrogel soft lens comprising fluorine-containing polyacrylate or polymethacrylate prepared by the above-described method of the present invention.

Molding into the soft lens of the present invention can be made by any conventional method, for example, can be produced by casting mold and spin coating method. The soft lens of the present invention exhibits excellent physical properties, in particular good water content and oxygen permeability.

Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are only for illustrating the present invention in more detail, it is to those of ordinary skill in the art that the scope of the present invention is not limited by these examples in accordance with the gist of the present invention. Will be self explanatory.

Example 1 Synthesis of 5-hydroxy-2,2,3,3,4,4-hexafluoropentyl methacrylate

In a 100 mL flask, 2 g (9.43 mmol) of 2,2,3,3,4,4-hexafluoro pentanediol (Aldrich) was dissolved in 50 mL of diethyl ether, followed by 0 ° C using an ice bath. After cooling with 2.86 g (28.3 mmol) triethyl amine was added and 1.08 g (10.37 mmol) methacryloyl chloride (Aldrich) was slowly added dropwise. After stirring for 1 hour at the same temperature, 30 ml of distilled water was added thereto, extracted with diethyl ether, and the water remaining in the organic layer was removed with sodium sulfate and concentrated. The resulting product was separated by flash column chromatography to yield 1.39 g of the desired compound (yield: 52.6%): ¹ H-NMR spectra (δ): 6.5-5.5 (2s, 2H, = CH ₂ ), 4.7 -4.5 (t, 2H, CF ₂ -CH ₂ -O), 4.3-4.0 (m, 2H, CF ₂ -CH ₂ -OH), 2.0 ppm (m, 4H, -CH ₃ , -OH)

Example 2: Synthesis of 6-hydroxy-2,2,3,3,4,4,5,5-octafluorohexyl methacrylate

In a 100 ml flask, 2 g (7.63 mmol) of 2,2,3,3,4,4,5,5-octafluoro hexanediol (Aldrich) was dissolved in 50 ml of diethyl ether, followed by ice bath. After cooling to 0 ° C., 2.32 g (22.89 mmol) of triethyl amine were added and 0.87 g (8.39 mmol) of methacryloyl chloride was slowly added dropwise, followed by the same procedure as in Example 1 to 1.28 g Obtained the desired compound (yield: 50.9%): ¹ H-NMR spectra (δ): 6.5-5.5 (2s, 2H, = CH ₂ ), 4.7-4.5 (t, 2H, CF ₂ -CH ₂ -O ), 4.3-4.0 (m, 2H, CF ₂ -CH ₂ -OH), 2.0 ppm (m, 4H, -CH ₃ , -OH)

Example 3: of 10-hydroxy-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecyl methacrylate synthesis

In a 100 mL flask, 2 g (4.33 mmol) of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro decandiol ( Aldrich) was dissolved in 50 mL of diethyl ether, then cooled to 0 ° C. using an ice bath, and then 1.31 g (13 mmol) of triethyl amine were added, and 0.5 g (4.76 mmol) of methacryloyl The chloride was slowly added dropwise followed by the same procedure as in Example 1 to yield 1.16 g of the desired compound (yield: 50.6%): ¹ H-NMR spectra (δ): 6.5-5.5 (2s, 2H, = CH ₂ ), 4.7-4.5 (t, 2H, CF ₂ -CH ₂ -O), 4.3-4.0 (m, 2H, CF ₂ -CH ₂ -OH), 2.5-2.0 ppm (m, 4H, -CH ₃ ,- OH)

Example 4: 1-hydroxy-2- (2,2,3,3,4,4,5,5-octafluorohexyloxy) ethyl methacrylate and 2-hydroxy-1- (2, Synthesis of 2,3,3,4,4,5,5-octafluorohexyloxy) ethyl methacrylate

2 g (7.63 mmol) of 2,2,3,3,4,4,5,5-octafluoro hexanediol (Aldrich) and 0.87 g (8.39 mmol) 1,2-dihydrate in a 100 mL flask Roxyethyl methacrylate (Aldrich) was dissolved in 50 ml of diethyl ether, then 2.1 g (8 mmol) triphenylphosphine (Aldrich) was added and 1.26 ml (8 mmol) of diethyl azodica Voxylate (Aldrich) was slowly added dropwise. Subsequently, after stirring for 1 hour at the same temperature, 30 ml of distilled water was added and extracted with diethyl ether, followed by removing water remaining in the organic layer with sodium sulfate and concentrating. Flash column chromatography on the thus obtained product gave 1.3 g of the desired mixture (yield: 50%): ¹ H-NMR spectra (δ): 6.5-5.5 (2s, 2H, = CH ₂ ), 4.7-4.5 ( t, 2H, CF ₂ -CH ₂ -O), 4.5-4.0 (m, 5H, CF ₂ -CH ₂ -O, O-CH-CH ₂ -O), 2.0 ppm (m, 4H, -CH ₃ , -OH)

Example 5: Synthesis of 2,2,3,3,4,4-hexafluoropentanediol dimethacrylate

In a 100 ml flask, 1 g (4.71 mmol) of 2,2,3,3,4,4-hexafluoro pentanediol was dissolved in 50 ml diethyl ether, and then cooled to 0 ° C. using an ice bath, followed by 4.77 g (47.1 mmol) triethyl amine was added and 2.46 g (23.6 mmol) methacryloyl chloride was slowly added dropwise followed by the same procedure as in Example 1 to yield 1.65 g of the desired compound (yield: 99.9 %): ¹ H-NMR spectra (δ): 6.5-5.5 (2s, 4H, 2 = CH ₂ ), 4.7-4.5 (t, 4H, 2 CF ₂ -CH ₂ -O), 2.0 ppm (s, 6H , 2 -CH ₃ )

Example 6: Preparation of Contact Lenses I

1 g of 2,2 synthesized in Example 5 as 9 g of 5-hydroxy-2,2,3,3,4,4-hexafluoropentyl methacrylate and a crosslinking agent synthesized in Example 1 above Dissolve 0.5 g of AIBN (Aldrich) as an initiator in a mixed solution of 3,3,4,4-hexafluoropentanediol dimethacrylate, and then inject into a mold made of polypropylene and in an oven at 110 ° C. Cured by polymerization for 30 minutes. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 53%, and the oxygen permeability was high as 33 DK.

Example 7 Preparation of Contact Lenses II

9 g of 6-hydroxy-2,2,3,3,4,4,5,5-octafluorohexyl methacrylate synthesized in Example 2 and 1 g synthesized in Example 5 as a crosslinking agent Was dissolved 0.2 g of AIBN as an initiator in a mixed solution of 2,2,3,3,4,4-hexafluoropentanediol dimethacrylate, and then injected into a mold made of polypropylene and placed in an oven at 110 ° C. Cured by polymerization for 40 minutes. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 55% and the oxygen permeability was high as 35 DK.

Example 8 Fabrication of Contact Lenses III

9.2 g of 10-hydroxy-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro synthesized in Example 3 above BPO (Aldrich) as an initiator in a mixed solution of 0.8 g of 2,2,3,3,4,4-hexafluoropentanediol dimethacrylate synthesized in Example 5 as a lodecyl methacrylate and a crosslinking agent 0.4 g was dissolved and then poured into a mold made of polypropylene and cured by polymerization in an oven at 90 ° C. for 40 minutes. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 58%, and the oxygen permeability was high as 38 DK.

Example 9 Fabrication of Contact Lenses IV

8 g of 1-hydroxy-2- (2,2,3,3,4,4,5,5-octafluorohexyloxy) ethyl methacrylate and 2-hydroxy synthesized in Example 4 above -1- (2,2,3,3,4,4,5,5-octafluorohexyloxy) ethyl methacrylate mixture, 2 g of 2,2,3 synthesized in Example 5 above as a crosslinking agent 0.4 g of AIBN as an initiator was dissolved in a mixed solution of 3,4,4-hexafluoropentanediol dimethacrylate, and then poured into a mold made of polypropylene and polymerized in an oven at 120 ° C. for 35 minutes to cure. I was. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 55% and the oxygen permeability was high as 35 DK.

Example 10 Fabrication of Contact Lenses V

9 g of 10-hydroxy-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro synthesized in Example 3 above Dissolve 0.5 g of AIBN as an initiator in a mixed solution of rhodesyl methacrylate and 1 g of ethylene glycol dimethacrylate (Aldrich), which is commonly used as a crosslinking agent, and then inject into a polypropylene mold. The mixture was cured by polymerization in an oven at 40 ° C. for 40 minutes. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 51% and the oxygen permeability was 30 DK.

Example 11: Fabrication of Contact Lens VI

7 g of 5-hydroxy-2,2,3,3,4,4-hexafluoropentyl methacrylate synthesized in Example 1, 2 g of 2-hydroxyethyl methacrylate (Aldrich) And 0.5 g of AIBN as an initiator was dissolved in a mixed solution of 1 g of ethylene glycol dimethacrylate as a crosslinking agent, and then injected into a mold made of polypropylene and polymerized in an oven at 120 ° C. for 40 minutes to cure. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 50%, and the oxygen permeability was 28 DK.

Example 12 Preparation of Contact Lenses

2 g of 5-hydroxy-2,2,3,3,4,4-hexafluoropentyl methacrylate synthesized in Example 1, 5 g of 2-hydroxyethyl methacrylate and 1 as a crosslinking agent 0.5 g of AIBN as an initiator was dissolved in a mixed solution of ethylene glycol dimethacrylate, then poured into a mold made of polypropylene, and cured by polymerization in an oven at 120 ° C. for 40 minutes. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 44%, and the oxygen permeability was 25 DK.

Comparative Example 1: Preparation of Contact Lenses

 9 g of 2-hydroxyethyl methacrylate and a crosslinking agent, which are widely used, are dissolved 0.5 g of AIBN as an initiator in a mixed solution of 1 g of ethylene glycol dimethacrylate, and then in a mold made of polypropylene. It was injected and cured by polymerization in an oven at 120 ° C. for 40 minutes. Subsequently, when the water content was measured by removing the lens from the mold, the water content was 37% and the oxygen permeability was low as 10 DK.

The present invention provides novel fluorine-containing acrylate or methacrylate monomers. The present invention also provides novel fluorine-containing diacrylate or dimethacrylate crosslinkers. On the other hand, the present invention provides novel fluorine-containing polyacrylates or polymethacrylates. The present invention provides a novel process for preparing fluorine-containing polyacrylates or polymethacrylates. The present invention also provides a hydrogel soft lens comprising a novel fluorine-containing polyacrylate or polymethacrylate. Since the novel fluorine-containing polyacrylates or polymethacrylates of the present invention are made from monomers having fluorine atoms and hydroxy groups at the same time, they exhibit excellent moisture content and oxygen permeability and are useful as materials for hydrogel soft lenses.

Claims (10)

A fluorine-containing acrylate or methacrylate monomer represented by Formula 3: Formula 3 In the above formula, R is H or CH ₃ and R 'is CH ₂ -CF ₂ -CF ₂ -CF ₂ -CF ₂ -CH ₃ . delete Method for preparing fluorine-containing polyacrylate or polymethacrylate, comprising the following steps: (a) preparing a mixed solution comprising the fluorine-containing monomer component of claim 1, a fluorine-containing crosslinking agent of Formula 5 and a radical initiator; And (b) supplying heat to the mixed solution to induce a thermal polymerization reaction. Formula 5 In the above formula, R is H or CH ₃ , Rff is C ₁ -C ₃₆ fluoro alkyl or C ₁ -C ₃₆ fluoro cycloalkyl, and a is an integer from 1-10. The method of claim 3, wherein the mixed solution is acrylic acid, methacrylic acid, acrylamide, N, N-dimethylacrylamide, methacrylamide, methyl methacrylate, 2-hydroxyethyl methacrylate, glyceryl methacrylate Fluorine-containing polyacryl, further comprising a hydrophilic monomer component selected from the group consisting of N-vinyl-2-pyrrolidone, α-methylene-N-methyl-pyrrolidone and 1-vinyl imidazole. Process for the production of latex or polymethacrylate 4. The radical initiator according to claim 3, wherein the radical initiator is azo bisisobutyronitrile, 2,2'-azo bis (2,4-dimethylpentanenitrile), 2,2'-azo bis (2,4-dimethylvalero Nitrile), benzoyl peroxide, di (secbutyl) peroxydicarbonate, and isopropylperoxydicarbonate, wherein the fluorine-containing polyacrylate or polymethacrylate is produced. 4. The fluorine-containing polyacrylate or polymethacrylate according to claim 3, wherein the mixed solution comprises 0.5-20 parts by weight of the crosslinking agent and 0.01-10 parts by weight of the initiator with respect to 100 parts by weight of the monomer component. Manufacturing method. The fluorine-containing polyacrylate or polymethacrylate of claim 6, wherein the mixed solution comprises 1-3 parts by weight of the crosslinking agent and 0.1-5 parts by weight of the initiator with respect to 100 parts by weight of the monomer component. Manufacturing method. The method of claim 4, wherein the weight ratio of the fluorine-containing monomer: hydrophilic monomer is 95: 5-10: 90. The method of claim 8, wherein the weight ratio of the fluorine-containing monomer: hydrophilic monomer is 95: 5-50: 50. A hydrogel soft lens comprising fluorine-containing polyacrylate or polymethacrylate prepared by the method of any one of claims 3 to 9.