WO2019132415A1 - Fluoropolymère, composition de fluoropolymère le contenant, et couche de fluoropolymère l'utilisant - Google Patents

Fluoropolymère, composition de fluoropolymère le contenant, et couche de fluoropolymère l'utilisant Download PDF

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WO2019132415A1
WO2019132415A1 PCT/KR2018/016329 KR2018016329W WO2019132415A1 WO 2019132415 A1 WO2019132415 A1 WO 2019132415A1 KR 2018016329 W KR2018016329 W KR 2018016329W WO 2019132415 A1 WO2019132415 A1 WO 2019132415A1
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fluoropolymer
range
chain alkyl
fluorinated
fluorine
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PCT/KR2018/016329
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Korean (ko)
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손은호
박인준
하종욱
이수복
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한국화학연구원
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Publication of WO2019132415A1 publication Critical patent/WO2019132415A1/fr
Priority to US16/913,016 priority Critical patent/US20200385563A1/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C08L33/16—Homopolymers or copolymers of esters containing halogen atoms

Definitions

  • Fluorine forms a strong carbon-fluorine bond because it has a high electron density, a small atomic radius next to hydrogen atoms, and strong electronegativity. Due to such fluorine properties, monomers containing a perfluoroalkyl group have a critical surface tension of as low as 6-8 dynes / cm, and surface energy is also very low, repelling both water and oil. As a result, the fluorine-based compound is superior in terms of chemical stability, heat resistance, weatherability, non-stickiness, low surface energy, water repellency and low refractive index.
  • fluorinated functional materials are widely used as core materials of next generation technologies in optical communication, optoelectronics, semiconductors, automobiles, and computers in high-tech industries because they exhibit excellent performance that can not be realized by other materials due to contamination resistance, weather resistance, heat resistance, .
  • fluorinated functional materials are widely used as core materials of next generation technologies in optical communication, optoelectronics, semiconductors, automobiles, and computers in high-tech industries because they exhibit excellent performance that can not be realized by other materials due to contamination resistance, weather resistance, heat resistance, .
  • an antifouling coating such as an outermost layer of a liquid crystal display or a frame of an elegant display
  • Fluoropolymers have properties such as low surface energy, water repellency, lubricity, and low refractive index, along with excellent heat resistance, chemical resistance and weather resistance, and have been widely used in industry, starting from household articles.
  • the present inventors have found that the present inventors have found that a fluoropolymer having excellent surface energy and light transmittance similar to that of a conventional fluoropolymer, exhibiting excellent pencil strength, exhibiting excellent adhesion to a substrate and coating stability, And has completed the present invention by confirming that it has the above functions.
  • An object of one aspect of the present invention is to provide a fluorine-based polymer having high pencil strength and low surface energy while exhibiting excellent solubility in a common organic solvent and adhesion to a substrate surface, and a fluorine-based polymer membrane using the same.
  • Another object of the present invention is to provide a fluoropolymer composition comprising the fluoropolymer.
  • R f is C 1-20 fluorinated straight chain alkyl or C 3-20 fluorinated branched chain alkyl
  • R 1-4 are each independently hydrogen (H), methyl (CH 3 ) or a halogen group
  • R 5 is C 1-20 straight chain alkyl or C 3-20 branched chain alkyl
  • x is in the range of 45 to 55, y is in the range of 30 to 40, p is in the range of 1-10, and q is in the range of 10-20;
  • fluorinated polymer composition comprising the fluorinated polymer represented by the above formula (1) and an organic solvent.
  • fluorinated polymer membrane comprising the fluorinated polymer represented by the above formula (1).
  • step 2 A step of coating the polymer solution of step 1 on a substrate and drying to form a polymer membrane (step 2).
  • optical film comprising the above fluorinated polymer membrane.
  • the fluorine-based polymer provided in one aspect of the present invention has low surface energy and high light transmittance, and can be applied to various applications requiring such properties.
  • the surface energy can be lowered to 19 mN / m or less and the light transmittance can be increased by more than 2%.
  • it has an effect of exhibiting excellent pencil strength.
  • the fluorine-based polymer provided in one aspect of the present invention can be applied as a surface coating and a membrane material for various products due to its high solubility in common organic solvents even though it has a very low surface energy.
  • the base material has excellent adhesion to the surface of the base material and is applicable to various fields such as automobile glass, building exterior material, fresh water, condenser in a power plant, and solar battery.
  • FIG. 1 is a graph of light transmittance of a fluorinated polymer membrane and a glass substrate (bare glass) prepared by using Examples 1 to 5;
  • FIG. 1 is a graph of light transmittance of a fluorinated polymer membrane and a glass substrate (bare glass) prepared by using Examples 1 to 5;
  • FIG. 1 is a graph of light transmittance of a fluorinated polymer membrane and a glass substrate (bare glass) prepared by using Examples 1 to 5;
  • FIG. 1 is a graph of light transmittance of a fluorinated polymer membrane and a glass substrate (bare glass) prepared by using Examples 1 to 5;
  • FIG. 1 is a graph of light transmittance of a fluorinated polymer membrane and a glass substrate (bare glass) prepared by using Examples 1 to 5;
  • FIG. 1 is a graph of light transmittance of a fluorinated polymer membrane and a glass substrate (bare glass) prepared by using Examples 1 to 5;
  • FIG. 1 is a graph of
  • FIG. 2 is a graph showing the pencil intensity of a polymer membrane prepared by using Examples 1 to 5 and Comparative Example 2.
  • FIG. 2 is a graph showing the pencil intensity of a polymer membrane prepared by using Examples 1 to 5 and Comparative Example 2.
  • R f is C 1-20 fluorinated straight chain alkyl or C 3-20 fluorinated branched chain alkyl
  • R 1-4 are each independently hydrogen (H), methyl (CH 3 ) or a halogen group
  • R 5 is C 1-20 straight chain alkyl or C 3-20 branched chain alkyl
  • x is in the range of 45 to 55, y is in the range of 30 to 40, p is in the range of 1-10, and q is in the range of 10-20;
  • the fluorinated polymer according to the present invention can be represented by the above formula (1).
  • R f may be represented by - (CH 2 ) a (CF 2 ) b -F.
  • a may be an integer in the range of 1 to 10, an integer in the range of 1 to 7, and an integer in the range of 1 to 3.
  • B may be an integer ranging from 1 to 15, an integer ranging from 1 to 10, an integer ranging from 1 to 5, and most preferably an integer ranging from 1 to 3.
  • R 1 , R 2 , R 3 and R 4 in the fluorine-containing polymer represented by Formula 1 may each independently be hydrogen (H), methyl (CH 3 ), and a halogen group.
  • the halogen group may be fluorine (F), chlorine (Cl).
  • R 1 , R 2 , R 3, and R 4 in the fluorine-containing polymer represented by Formula 1 are methyl.
  • R 5 in the fluorine-containing polymer represented by Formula 1 may be represented by - (CH 2 ) c -CH 3 .
  • c may be an integer ranging from 0 to 15, an integer ranging from 1 to 10, and an integer ranging from 1 to 5, but the range of the value c is not limited thereto.
  • the above x is preferably 45-55, more preferably 46-54, most preferably 47-50.
  • the above-mentioned y is preferably 30-40, more preferably 32-38, most preferably 34-36.
  • p + q may be 30 or less, and may be 25 or less.
  • p is preferably 1-10, may be 1-8, may be 1-5, may be 1-3, and may be 2-3. Or more, it is possible to exhibit excellent tackiness upon coating the substrate.
  • q is preferably 10-20, may be 12-18, and may be 14-16.
  • the fluorine-containing polymer according to the present invention can be used to form a stable polymer membrane through a curing process.
  • the number average molecular weight of the fluorinated polymer represented by Formula 1 is preferably 5,000 to 500,000, and more preferably 10,000 to 400,000. If the number average molecular weight of the fluorinated polymer is less than 5,000, the thermal and mechanical strength of the polymer may be decreased. If the number average molecular weight is more than 500,000, the solubility of the fluorinated polymer in the organic solvent may rapidly decrease.
  • the polymer represented by the general formula (1) provided in one aspect of the present invention can dissolve in a generally known organic solvent unlike the conventional fluorine-based polymer, and thus has a very advantageous effect in the manufacturing process.
  • organic solvent include organic solvents such as chloroform, dichloromethane, acetone, pyridine, tetrahydrofuran, chlorobenzene, and dichlorobenzene.
  • fluorine-based polymer provided in one aspect of the present invention may be represented by the following general formula (2).
  • R f is C 1-20 fluorinated straight chain alkyl or C 3-20 fluorinated branched chain alkyl
  • R 1 , R 2 ', R 2 ", R 3 and R 4 are each independently hydrogen (H), methyl (CH 3 ) or a halogen group;
  • R 5 ' is C 2-20 straight chain alkyl or C 3-20 branched chain alkyl
  • x 45 to 55, y 'is 22 to 28, y " is 8 to 12, p is 1 to 10, and q is 10-20;
  • R f may be represented by - (CH 2 ) a (CF 2 ) b -F.
  • a may be an integer in the range of 1 to 10, an integer in the range of 1 to 7, and an integer in the range of 1 to 3.
  • B may be an integer ranging from 1 to 15, an integer ranging from 1 to 10, an integer ranging from 1 to 5, and most preferably an integer ranging from 1 to 3.
  • R 1 , R 2 ', R 2 ", R 3 and R 4 in the fluorine-containing polymer represented by Formula 2 may each independently be hydrogen (H), methyl (CH 3 )
  • the halogen group may be fluorine (F), chlorine (Cl).
  • R 1 , R 2 ', R 2 ", R 3 and R 4 in the fluorine-containing polymer represented by Formula 1 are methyl.
  • R 5 ' may be represented by - (CH 2 ) d -CH 3 .
  • d may be an integer ranging from 1 to 15, an integer ranging from 1 to 10, and an integer ranging from 1 to 5, but the range of the d value is not limited thereto.
  • the above x is preferably 45-55, more preferably 6-54, most preferably 47-50.
  • y '+ y' ' is preferably 30-40, more preferably 32-38, most preferably 34-36.
  • p + q may be 30 or less, and may be 25 or less.
  • p is preferably 1-10, may be 1-8, may be 1-5, may be 1-3, and may be 2-3. Or more, it is possible to exhibit excellent tackiness upon coating the substrate.
  • q is preferably 10-20, may be 12-18, and may be 14-16.
  • the fluorine-containing polymer according to the present invention can be used to form a stable polymer membrane through a curing process.
  • a fluorinated polymer composition comprising the fluorinated polymer represented by Formula 1 or the fluorinated polymer represented by Formula 2 and an organic solvent.
  • the fluorine-based polymer is as described above, and the fluorine-based polymer according to the present invention has low surface energy and high light transmittance, and can be applied to various applications requiring such properties.
  • the organic solvent may be chloroform, dichloromethane, acetone, pyridine, tetrahydrofuran, chlorobenzene, dichlorobenzene or the like, but the organic solvent is not limited thereto.
  • fluorinated polymer membrane comprising the fluorinated polymer represented by the formula (1) or the fluorinated polymer represented by the formula (2).
  • the fluorinated polymer membrane provided in one aspect of the present invention can exhibit very low surface energy and excellent light transmittance. In addition, it has excellent adhesion to the surface of the substrate and can be cured, and thus it can be applied to various fields such as glass for automobiles, building exterior materials, condensers in fresh water or power plants, and solar cells.
  • step 2 A step of coating the polymer solution of step 1 on a substrate and drying to form a polymer membrane (step 2).
  • step 1 is a step of preparing a polymer solution by dissolving the fluorinated polymer as described in the present invention in an organic solvent.
  • the fluorine-based polymer according to the present invention has excellent solubility with an organic solvent and can be easily dissolved in an organic solvent to prepare a polymer solution.
  • the organic solvent used in step 1 may be chloroform, dichloromethane, acetone, pyridine, tetrahydrofuran, chlorobenzene, dichlorobenzene or the like, but the organic solvent is not limited thereto.
  • step 2 is a step of coating the polymer solution of step 1 on the substrate and drying to form a polymer membrane.
  • the application of the step 2 may be performed by a method such as spin coating, dip coating, roll coating and spray coating.
  • An optical film comprising the above fluorinated polymer membrane is provided.
  • the optical film may have a structure in which fluorine-based polymer membranes having different transmittances by region (wavelength region) of light are laminated alone or in combination.
  • the optical film may further include a non-fluorinated polymer membrane.
  • the fluorine-containing polymer represented by Formula 1 Organic solvent; And at least one selected from the group consisting of pigments, pigments, dyes, and additives.
  • Example 2 Polymerization was carried out under the same reaction conditions as in Example 1, and the content, number average molecular weight and dispersity of the reactants used for preparing the fluoropolymer of Example 2 are shown in Table 2 below.
  • Example 3 Polymerization was carried out under the same reaction conditions as in Example 1, and the content, number average molecular weight and dispersity of the reactants used for preparing the fluoropolymer of Example 3 are shown in Table 3 below.
  • Example 4 Polymerization was carried out under the same reaction conditions as in Example 1, and the content, number average molecular weight and dispersity of the reactants used for preparing the fluoropolymer of Example 4 are shown in Table 4 below.
  • Example 5 Polymerization was carried out under the same reaction conditions as in Example 1, and the content, number average molecular weight and dispersity of the reactants used for preparing the fluoropolymer of Example 5 are shown in Table 5 below.
  • PMMA Polymethyl methacrylate
  • the fluoropolymers prepared in Examples 1 to 5 were dissolved in chloroform (CDCl 3 ), and then nuclear magnetic resonance spectroscopy (NMR, Bruker AC 500P < 1 > H NMR spectrometer). The results are shown in Table 7 below. The composition of the polymer was calculated from the peak area ratio of the graph analyzed by nuclear magnetic resonance spectroscopy. The results are shown in Table 7.
  • Example 1 20: 20: 40: 5: 15 21: 23: 37: 2: 16
  • Example 2 30: 20: 30: 5: 15 29: 21: 29: 6: 15
  • Example 3 40: 20: 20: 5: 15 42: 19: 19: 3: 17
  • Example 4 50: 20: 10: 5: 15 48: 24: 11: 2: 15
  • polymers prepared in Examples 1 to 5 and Comparative Example 1 were dissolved in chloroform at a concentration of 2% by weight, dropped on a cleaned glass slide having a diameter of 1.5 cm, and dried at a rate of 3,000 rpm for 40 seconds
  • Polymer membranes were prepared for surface roughness, contact angle and surface energy evaluation by spin coating at the application time and drying at room temperature for 12 hours in a vacuum oven.
  • the surface roughness of the polymer membranes prepared above was measured using an atomic force microscope (Model: SPA 400, manufactured by Seiko Instruments Industry, Co., Ltd., Japan), and the results are shown in Table 8 below.
  • the contact angles of the prepared polymer membranes were measured using a contact angle meter (Kruss DSA10, Germany), and the contact angles measured by dropping water and diiodomathane (DMI) on the polymer membranes were shown in Table 7 Respectively.
  • spherical droplets lose their shape on the solid surface and exhibit hydrophilic properties that wet the surface.
  • spherical droplets exhibit hydrophobicity that flows easily along the external force without wetting the surface while maintaining the shape of the spheres on the solid surface.
  • the surface energy of the polymer membranes prepared above was calculated. Specifically, the surface energy was calculated using the Owens-Wendt-Rabel-Kaelble method after measuring the contact angle using water and a diiodomathane (DMI) solvent.
  • DMI diiodomathane
  • the contact angle of the polymer membrane prepared in Comparative Example 1 to water was 75.6 °, while the contact angle of the fluorinated polymer membrane of the present invention was 97 ° to 104.5 °.
  • the contact angle with respect to DMI it was confirmed that the polymer membrane prepared in Comparative Example 1 was 35.1 °, while the contact angle of the fluorinated polymer membrane in Examples 1 to 5 was remarkably excellent from 63.9 ° to 81.2 °.
  • the surface energy of the polymer membrane prepared in Comparative Example 1 was 44.3 mN / m, while the surface energies of the fluorine-based polymer membranes of Examples 1 to 4 were 17.4 mN / m to 26.7 mN / m, which is very low.
  • the surface energy of the fluorinated polymer membrane of Example 5 is PTFE (surface energy ⁇ 18 mN / m), which is known to have a very low surface energy, and a much lower number of cations.
  • the light transmittance of the fluorinated polymer membrane prepared using the fluorinated polymers of Examples 1 to 5 and the glass substrate (bare glass) was measured using a Varian Cary 5000 spectrometer ) In a wavelength range of 200 nm to 800 nm, and the results are shown in FIG.
  • the transmittance of the fluorinated polymer membrane obtained in Example 4 was far superior to that of the glass substrate and other fluorinated polymer membranes.
  • the transmittance was excellent in the wavelength range of 350 nm to 700 nm, and the transmittance was much better in the wavelength range of 450 nm to 600 nm.
  • the pencil hardness of the polymer membrane prepared using the fluorinated polymer of Examples 1 to 5 and the PMMA polymer of Comparative Example 2 was measured using a hardness analyzer (BGD 506, Biuged Instruments Co., Ltd., Guangzhou), and the results are shown in Fig.
  • composition range of the fluorine-based polymer was far superior to that of the fluorine-based polymer membranes obtained in Examples 1, 2, 3 and 5 in which the x value was outside the range of 45-55.
  • the fluorine-based polymer according to the present invention has low surface energy and high light transmittance, and can be applied to various applications requiring such properties.
  • the surface energy can be lowered to 19 mN / m or less when the glass is coated, and the light transmittance can be increased by 2% or more.
  • the pencil strength showed a value of F (5), and it was confirmed that the pencil strength was much superior to that of the PMMA polymer and other fluorinated polymers.
  • it is excellent in light transmittance and pencil strength and can be widely applied as an optically applied material (optical film).
  • the fluorine-based polymer according to the present invention has a very low surface energy upon coating, it can be applied to surface coatings and membrane materials of various products due to high solubility in common organic solvents. Further, it is excellent in adhesion to the surface of the substrate and can be cured, which is applicable to various fields such as automobile glass, building exterior material, condenser in a fresh water or a power plant, a solar cell, and a light collector.

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Abstract

Selon un aspect, la présente invention concerne un fluoropolymère représenté par la formule 1. Le fluoropolymère selon un aspect de la présente invention peut présenter une faible énergie superficielle et un facteur élevé de transmission de la lumière, et peut donc s'appliquer à diverses applications exigeant de telles propriétés. En particulier, après application sur du verre, l'énergie superficielle peut être abaissée à 19 mN/m au maximum, et le facteur de transmission de la lumière peut être augmenté de plus de 2 %. En même temps, le fluoropolymère possède la qualité de présenter une excellente dureté au crayon. De plus, le fluoropolymère selon un aspect de la présente invention peut s'utiliser comme matériau de revêtement de surface et matériau de membrane pour différents produits, du fait de sa grande solubilité dans les solvants organiques usuels, même s'il présente une très faible énergie superficielle. En outre, le polymère présente une excellente adhérence à la surface d'un matériau de base et peut être soumis à un traitement de durcissement, de sorte que le fluoropolymère peut s'appliquer à diverses applications telles qu'une vitre d'automobile, un matériau extérieur pour bâtiments, l'eau douce, les condenseurs dans les centrales, et les batteries solaires, etc.
PCT/KR2018/016329 2017-12-26 2018-12-20 Fluoropolymère, composition de fluoropolymère le contenant, et couche de fluoropolymère l'utilisant WO2019132415A1 (fr)

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KR1020180142481A KR102144814B1 (ko) 2017-12-26 2018-11-19 불소계 고분자, 이를 포함하는 불소계 고분자 조성물 및 이를 이용한 불소계 고분자막
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JP2002097338A (ja) * 2000-09-22 2002-04-02 Nof Corp 樹脂組成物およびその成形物
JP2006063132A (ja) * 2004-08-25 2006-03-09 Fuji Photo Film Co Ltd 有機溶剤系塗布改良剤
KR101212572B1 (ko) * 2012-06-18 2012-12-14 (주)아해 내오존성이 우수한 콘크리트 구조물의 표면 도장공법
JP2013173840A (ja) * 2012-02-24 2013-09-05 Nof Corp 硬化性樹脂組成物及びその硬化成形物
WO2017216201A1 (fr) * 2016-06-17 2017-12-21 Merck Patent Gmbh Polymères fluorés

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002097338A (ja) * 2000-09-22 2002-04-02 Nof Corp 樹脂組成物およびその成形物
JP2006063132A (ja) * 2004-08-25 2006-03-09 Fuji Photo Film Co Ltd 有機溶剤系塗布改良剤
JP2013173840A (ja) * 2012-02-24 2013-09-05 Nof Corp 硬化性樹脂組成物及びその硬化成形物
KR101212572B1 (ko) * 2012-06-18 2012-12-14 (주)아해 내오존성이 우수한 콘크리트 구조물의 표면 도장공법
WO2017216201A1 (fr) * 2016-06-17 2017-12-21 Merck Patent Gmbh Polymères fluorés

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