WO2020235846A1 - Matériau hybride de silice fluorée durcissable aux uv, hautement transparent et amphiphobe ayant des propriétés anti-traces de doigts et anti-salissures - Google Patents

Matériau hybride de silice fluorée durcissable aux uv, hautement transparent et amphiphobe ayant des propriétés anti-traces de doigts et anti-salissures Download PDF

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WO2020235846A1
WO2020235846A1 PCT/KR2020/006184 KR2020006184W WO2020235846A1 WO 2020235846 A1 WO2020235846 A1 WO 2020235846A1 KR 2020006184 W KR2020006184 W KR 2020006184W WO 2020235846 A1 WO2020235846 A1 WO 2020235846A1
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carbon atoms
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fluorinated silica
hybrid material
formula
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Korean (ko)
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하창식
정극민
박성수
쿠민밍
장용수
민구오콴
리앙롱난
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부산대학교 산학협력단
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances

Definitions

  • the present invention relates to an amphiphilic fluorinated silica hybrid material having anti-fingerprint and antifouling properties, and in particular, an amphiphilic fluorinated silica hybrid material comprising fluorinated silica particles, thiol-based compounds, polysiloxane monomers, photoinitiators and solvents, and It relates to a manufacturing method.
  • Hybrid materials having anti-fingerprint, hydrophobicity, oil-repellency and antifouling properties have high potential applications in various industries such as textiles, construction, automobiles, and electronic products, and have been actively studied in recent years.
  • the method of controlling the properties of the surface can be controlled by controlling the chemical treatment and the surface structure of the surface.
  • the contact angle reaches 150° to 170° and can be applied as a material that prevents surface contamination.
  • the coating surface has both hydrophobic and oleophobic properties, and is amphiphilic [amphiphobic (water and oil). repellent)] is expected to be solved through the development of materials.
  • the amphiphilic property can be solved through the control of the chemical composition and surface structure of the material surface.
  • hydrophobic groups such as alkyl groups, phenyl groups, halogenated alkyl groups, long chain hydrocarbon groups, hydroxy groups, carboxyl groups, amino groups, etc. having hydrophilic properties, and hydrophilic groups (oleophobic groups) are appropriately introduced into the material.
  • a surface having amphiphilic properties can be realized, and the surface energy can be lowered through an alkyl compound containing a fluorine group to improve the amphiphilic properties, and the formation of a siloxane (Si-O-Si) bond such as an organic siloxane can be achieved. Because it has the properties of inorganic materials such as glass, the durability of the material can be improved.
  • UV curable polymers including organic optical resins through such hybrids have been extensively studied for optical applications. Accordingly,'Korea Patent Registration No. 10-1129258' relates to a UV curable coating composition and coating film, which can prevent adhesion of contamination such as fingerprint traces, can be easily removed, and impart contamination resistance and abrasion resistance at the same time. Therefore, it is disclosed that it can be applied to a variety of substrates due to its excellent water repellency, oil repellency and antifouling properties, and excellent adhesion to the substrate while maintaining its properties continuously. However, the contents of the flexibility, impact strength and transparency of the film are disclosed. Since it is not described, various problems are found to be applied to actual application fields.
  • an object of the present invention is to provide an amphiphilic fluorinated silica hybrid material having excellent effects on transparency, anti-fingerprint, hydrophobicity, oil waterproofing and antifouling properties.
  • Fluorinated silica particles in which a fluorine monomer is connected to the silica particles
  • the A is a thiol-based compound having 1 to 4 thiol groups
  • the R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms,
  • R 4 is a compound having a fluorine group:
  • R 4 is a C 1 to C 3 alkyl group or a C 6 to C 12 aryl group
  • R 5 and R 6 are each independently a vinyl group or an alkyl group having 1 to 3 carbon atoms
  • n is an integer of 1 to 200,000
  • m is an integer of 1 to 20,000.
  • Fluorinated silica particles in which a fluorine monomer is connected to the silica particles
  • Thiol-based compounds such as trimethylolpropane tris(3-mercaptopropionate) (TMPTMP) or pentaerythritol tetrakis(3-mercaptopropionate) (PETTMP);
  • the R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms,
  • R 4 is a compound having a fluorine group.
  • It provides a method for producing an amphiphilic fluorinated silica hybrid material comprising; a fifth step of stirring by adding a photoinitiator to the additive.
  • the present invention provides an amphiphilic fluorinated silica hybrid material containing fluorinated silica particles, thiol-based compounds, polysiloxane monomers, photoinitiators, and solvents, thereby providing transparency, anti-fingerprint, hydrophobicity, flexibility, oil for coating materials applied in various industries. It has excellent effects on waterproof and antifouling properties.
  • FIG. 1 shows a chemical reaction process for preparing fluorinated silica according to an embodiment of the present invention.
  • FIG. 2 shows a chemical reaction process for preparing an amphiphilic fluorinated silica hybrid material according to an embodiment of the present invention.
  • FIG 3 is a graph showing the transparency of a silica hybrid material sample according to an embodiment of the present invention through a UV-vis spectrum.
  • FIG. 4 is a photograph showing the result of contact angles of moisture, oil, and artificial fingerprints on a coated surface according to an embodiment of the present invention.
  • FIG. 5 is a photograph showing moisture, oil and artificial fingerprint contact angle results on a coated surface according to an embodiment and a comparative example of the present invention.
  • FIG. 6 is a photograph showing a result of a fingerprint removal test on a coated surface according to an embodiment and a comparative example of the present invention.
  • FIG. 7 is a photograph showing a result of a flexibility test of a coated PET film according to an embodiment of the present invention.
  • FIG. 8 is a photograph showing the antifouling properties of the coated glass surface according to an embodiment of the present invention.
  • silica particles produced by hydrolysis and condensation reactions Fluorinated silica particles in which a fluorine monomer is connected to the silica particles; Thiol-based compounds having 1 to 4 thiol groups; Polysiloxane monomers; Photoinitiators; And a solvent; and provides an amphiphilic fluorinated silica hybrid material represented by the following Formula 1:
  • A is a thiol-based compound having 1 to 4 thiol groups
  • B is a polysiloxane monomer represented by the following Formula 2
  • R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or It is a C6-C14 aryl group
  • R 4 is a compound having a fluorine group:
  • R 4 is an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 12 carbon atoms
  • An alkyl group is an atomic group represented by the general formula of C n H 2n+1 by removing one hydrogen atom from a chain or saturated aliphatic hydrocarbon.
  • An aryl group corresponds to an alkyl group in which one hydrogen atom has been removed from an aromatic hydrocarbon and one hydrogen atom has been removed from the aliphatic hydrocarbon.
  • phenyl group C 6 H 5 -
  • anthryl group C 14 H 9 -
  • phenanthryl group C 14 H 9 -
  • Thiol-based compounds are 2,2′-(ethylenedioxy)diethanethiol (2,2′-(Ethylenedioxy)diethanethiol), 1,6-hexanedithiol (1,6-Hexanedithiol), 2,5-hexanedithiol Ol (2,5-Hexanedithiol), benzene-1,4-dithiol (Benzene-1,4-dithiol), 1,3-propanedithiol (1,3-Propanedithiol), 1,2-ethanedithiol ( 1,2-Ethanedithiol), trimethylolpropane tris (3-mercaptopropionate) (Trimethylolpropane tris (3-mercaptopropionate), TMPTMP), pentaerythritol tetrakis (3-mercaptopropionate) (Pentaerythritol tetrakis ( It is preferably any one selected from the
  • a thiol-based compound is a compound having an SH group, that is, a thiol group, and has a reducing power, and is oxidized by itself to become a compound having a disulfide bond (S-S bond).
  • S-S bond disulfide bond
  • trimethylolpropanetris and pentaerythritol tetrakis are SH groups in which oxygen in OH is replaced with sulfur and have a mercapto group, a monovalent substituent, and play a role in improving the water repellency and oleophobicity of the coating film. do.
  • Siloxane is a generic term for a compound composed of silicon, oxygen, and hydrogen among compounds including Si-O bonds (siloxane bonds), and the chain of such siloxane bonds is called polysiloxane.
  • polysiloxane is also a generic term for a polymer compound having a siloxane bond.
  • the siloxane bond has good elasticity due to its flexible bonding angle, and the compound produced by this bond is soft and flexible and has high elasticity, so it can be used for various purposes.
  • the siloxane contained in the polysiloxane monomers can improve the durability of the material, and the methyl group contained at the end of the monomer is a non-polar group and has hydrophobic properties.
  • the silica particles of the present invention may be represented by the following formula (3).
  • R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms.
  • the silica particles may be produced by a hydrolysis reaction and a condensation reaction through a sol-gel method, which is one of the powder preparation methods of organic or inorganic oxides.
  • the sol-gel reaction is a reaction in which a sol obtained by hydrolysis is desolvated and then a dry gel is formed through an additional reaction.
  • Fluorinated silica particles can be prepared by connecting a fluorine monomer to the surface of the silica particles produced by this reaction.
  • the fluorinated silica particles of the present invention may be represented by the following formula (4).
  • R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms, and R 4 is a compound having a fluorine group.
  • an acrylic organic compound containing a UV-curable thiol group and a siloxane that is, an organic compound mixed with a thiol-based compound and a polysiloxane monomer, is mixed with fluorinated silica particles to provide excellent hardness and transparency, and heat resistance, anti-fingerprint and anti-fouling properties.
  • a hybrid material can be manufactured.
  • the hybrid material of the present invention may have high amphiphilic (hydrophobicity and oleophobicity) properties with a small amount of fluorine, and hardness and transparency may be greatly improved by appropriately dispersed silica particles in an organic compound.
  • the photoinitiator is preferably contained in an amount of 0.1 to 2.0% by weight based on the total weight of the fluorinated silica particles, the thiol-based compound, and the polysiloxane monomer mixture.
  • Photoinitiators include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzophenone, benzyl ketone, 2-chloro-thioxanthone, 2,4-diethyl-thioxanthone, diethoxyacetophenone, benzyl methyl ketal, 2-hydroxy- 2-methyl-1-phenyl-1-propanone and the like may be used.
  • the solvent is preferably any one selected from the group consisting of toluene, acetone, acetonitrile, ethyl acetate, dimethylacetamide, and mixtures thereof.
  • the solvent has a characteristic of good dissolving due to the polarity of the fluorinated silica particles, thiol compounds, and polysiloxane monomers.
  • the reaction is easy when the material is sufficiently dissolved in the solvent, and a clean and highly transparent surface can be obtained without coagulation during coating.
  • Ethyl acetate in the solvent is produced by distilling under heating after adding a small amount of sulfuric acid to acetic acid and ethanol.
  • it has strong power to dissolve various organic substances, it is important as a raw material for synthesizing organic compounds and is widely used as a solvent.
  • it is used as a fragrance, such as fruit juice and confectionery, and is not included in environmental regulations due to its low toxicity compared to general organic solvents, and can be used as a pharmaceutical raw material or pharmaceutical preparation such as antipyrine and atavrin.
  • Ethyl acetate has a relatively low boiling point of 77°C, which is similar to that of alcoholic organic solvents (ethanol, methanol, etc.), and because of this, hardening occurs quickly, so it is easy to remove the solvent after coating on various materials. In addition, it can be used as a role of controlling the viscosity that can be increased when the thiol-based compound and the polysiloxane monomer are combined.
  • silica particles produced by hydrolysis and condensation reactions Fluorinated silica particles in which a fluorine monomer is connected to the silica particles; Thiol, which is trimethylolpropane tris (3-mercaptopropionate) (TMPTMP) or pentaerythritol tetrakis (3-mercaptopropionate) (PETTMP) System compound; (Acryloxypropyl)methylsiloxane homopolymer (APMS) or [4-6% (methacryloxypropyl) methylsiloxane] dimethylsiloxane copolymer ([4-6% (Methacryloxypropyl) methylsioxane] dimethylsiloxane, MAPMS), a polysiloxane monomer; Photoinitiators; And a solvent; and provides an amphiphilic fluorinated silica hybrid material represented by the following Formula 5 or Formula 6:
  • R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms, and R 4 is a compound having a fluorine group.
  • trimethylolpropanetris and pentaerythritol tetrakis are SH groups in which oxygen in OH is replaced with sulfur and have a mercapto group, a monovalent substituent, and play a role in improving the water repellency and oleophobicity of the coating film. do.
  • the siloxane contained in the polysiloxane monomers can improve the durability of the material, and the methyl group contained at the end of the monomer is a non-polar group and has hydrophobic properties.
  • Photoinitiators include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzophenone, benzyl ketone, 2-chloro-thioxanthone, 2,4-diethyl-thioxanthone, diethoxyacetophenone, benzyl methyl ketal, 2-hydroxy- 2-methyl-1-phenyl-1-propanone and the like may be used.
  • the solvent is preferably any one selected from the group consisting of toluene, acetone, acetonitrile, ethyl acetate, dimethylacetamide, and mixtures thereof.
  • the solvent has a characteristic of good dissolving due to the polarity of the fluorinated silica particles, thiol compounds, and polysiloxane monomers.
  • the reaction is easy when the material is sufficiently dissolved in the solvent, and a clean and highly transparent surface can be obtained without coagulation during coating.
  • a first step of preparing silica particles by mixing a silica precursor and a silica monomer in a solvent A second step of adding and stirring a fluorine monomer and a photoinitiator to the mixture; A third step of preparing fluorinated silica particles by crosslinking silica particles and a fluorine monomer by irradiating ultraviolet rays on the stirred result; A fourth step of adding a thiol-based compound and a polysiloxane monomer to the fluorinated silica particles; And it provides a method for producing an amphiphilic fluorinated silica hybrid material comprising; a fifth step of stirring by adding a photoinitiator to the additive.
  • Thiol-based compounds are 2,2′-(ethylenedioxy)diethanethiol (2,2′-(Ethylenedioxy)diethanethiol), 1,6-hexanedithiol (1,6-Hexanedithiol), 2,5-hexanedithiol Ol (2,5-Hexanedithiol), benzene-1,4-dithiol (Benzene-1,4-dithiol), 1,3-propanedithiol (1,3-Propanedithiol), 1,2-ethanedithiol ( 1,2-Ethanedithiol), trimethylolpropane tris (3-mercaptopropionate) (Trimethylolpropane tris (3-mercaptopropionate), TMPTMP), pentaerythritol tetrakis (3-mercaptopropionate) (Pentaerythritol tetrakis ( It may be any one selected from the group
  • a thiol-based compound is a compound having an SH group, that is, a thiol group, and has a reducing power, and is oxidized by itself to become a compound having a disulfide bond (S-S bond).
  • S-S bond disulfide bond
  • trimethylolpropanetris and pentaerythritol tetrakis are SH groups in which oxygen in OH is replaced with sulfur and have a mercapto group, a monovalent substituent, and play a role in improving the water repellency and oleophobicity of the coating film. do.
  • the polysiloxane monomer of the present invention may be represented by the following formula (2).
  • R 4 is an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 12 carbon atoms
  • the solvent may be any one selected from the group consisting of toluene, acetone, acetonitrile, ethyl acetate, dimethylacetamide, and mixtures thereof.
  • the solvent has a characteristic of good dissolving due to the polarity of the fluorinated silica particles, thiol compounds, and polysiloxane monomers.
  • the reaction is easy when the material is sufficiently dissolved in the solvent, and a clean and highly transparent surface can be obtained without coagulation during coating.
  • the fluorinated silica particles of the present invention may be represented by the following formula (4).
  • R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms, and R 4 is a compound having a fluorine group.
  • TMMS trimethoxymetylsiane
  • HDTMS hexadecyltrimethoxysiane
  • TMPS trimethoxyphenylsilane
  • BTMS isobutyl (trimethoxy)silane
  • trimethoxysilan (MPTMS) 1.5 mmol of trimethoxysilan (MPTMS) was added to each flask, and then stirred at room temperature in the presence of nitrogen for about 24 to 48 hours.
  • MPTMS trimethoxysilan
  • HFA 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12-heneicosafluorododecyl acrylate
  • HFA benzoin ethyl ether
  • BEE benzoin ethyl ether
  • -SH sulfur group
  • PETTMP pentacrythritol tetrakis (3-mercaptopropionate)
  • TMMS trimethoxymetylsiane
  • HDTMS hexadecyltrimethoxysiane
  • TMPS trimethoxyphenylsilane
  • NO.4 A hybrid material sample prepared using NO.3 and Isobutyl(trimethoxy)silane (BTMS) was designated as NO.4.
  • the artificial fingerprint solution is a mixture of artificial sweat solution (lactic acid 3 ml/L, acetic acid 5 ml/L, sodium chloride 10 g/L, sodium hydrogen phosphate 10 g/L and DI water 1L) and 1-methoxy-2
  • An artificial fingerprint solution was prepared by mixing -propanol and hydroxyl terminated polydimethlsiloxane in a weight ratio of 3:3:4.
  • Sample No. 1 was coated on a glass substrate to imprint the actual fingerprint on the surface and erase it.
  • the artificial fingerprint solution was prepared by mixing artificial sweat solution, 1-methoxy-2-propanol, and hydroxyl terminated polydimethlsiloxane in a 3: 3: 4 weight ratio.
  • a conventional coating material was coated on a glass substrate to imprint an actual fingerprint on the surface and erase it.
  • a silica hybrid material containing a fluorine group was synthesized and prepared according to Examples 1 to 2, and the chemical reaction process and the synthesized compound for preparing a fluorinated silica hybrid material including trimethoxymetylsiane (TMMS) are shown in FIGS. 1 to 2.
  • TMMS trimethoxymetylsiane
  • Fig. 4 shows the results of measuring moisture, oil and artificial fingerprint contact angles of Samples No. 1 to No. 4.
  • the water contact angle 135°, the oil contact angle 100°, and the artificial fingerprint contact angle 102° showed the best amphiphilic properties.
  • Figure 5 shows the results of measuring moisture, oil, and contact angles of artificial fingerprints on a glass substrate coated with Sample No. 1 and a conventional coating material, which showed the best hydrophobicity and oleophobicity in Examples. As a result, each contact angle was the largest in Sample No. 1, and it was confirmed that the amphiphilic properties were superior to those of conventional coating materials.
  • Fig. 6 shows the results of performing a test in which an actual fingerprint is imprinted on a glass surface coated with Sample No. 1, a glass surface coated with a conventional coating material, and a general glass surface without any treatment on the surface.
  • Fig. 7 shows the results of performing a flexibility test after coating Sample No. 1 on a PET film. As a result, it was confirmed that even though it was coated on a PET film, one of the polymer films having excellent flexibility, the flexibility was maintained while showing high transparency without change.
  • Sample No. 1 was coated on a glass substrate and then soil and water were sprayed to confirm the antifouling properties. As a result, it was confirmed that the part coated with Sample No. 1 had hydrophobicity and oleophobicity, so that even if foreign substances such as soil were stained, it was neatly washed when washing with water.

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Abstract

La présente invention concerne un matériau hybride de silice fluorée amphiphobe ayant des propriétés anti-traces de doigts et anti-salissures et, en particulier, un matériau hybride de silice fluorée amphiphobe comprenant des particules de silice fluorée, un composé à base de thiol, un monomère polysiloxane, un photo-initiateur et un solvant, ainsi qu'un procédé de préparation associé. La présente invention concerne un matériau hybride de silice fluorée amphiphobe qui peut être appliqué à divers domaines et présente une transparence, des propriétés anti-traces de doigts, une hydrophobicité, une flexibilité, des propriétés d'étanchéité à l'huile et à l'eau et des propriétés anti-salissures.
PCT/KR2020/006184 2019-05-20 2020-05-11 Matériau hybride de silice fluorée durcissable aux uv, hautement transparent et amphiphobe ayant des propriétés anti-traces de doigts et anti-salissures WO2020235846A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114736614A (zh) * 2022-05-11 2022-07-12 深圳市创新精细玻璃有限公司 一种环保型oca光学胶及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6998425B2 (en) 2003-12-23 2006-02-14 General Electric Company UV curable coating compositions and uses thereof
KR101129258B1 (ko) 2009-12-21 2012-03-26 (주)금강엔터프라이즈 Ｕｖ 경화형 코팅 조성물 및 코팅 필름

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ÇAKMAKÇI , E. ET AL.: "UV-curable fluorine-containing hybrid coatings via thiol-ene ''click'' reaction and an in situ sol-gel method", POLYM. BULL., vol. 70, no. 3, 10 October 2012 (2012-10-10), pages 1037 - 1048, XP055762954 *
JEONG, K.-M. ET AL.: "Highly transparent, organic-inorganic hybrid UV-curable coating materials with amphiphobic characteristics", PROGRESS IN ORGANIC COATINGS, vol. 134, 22 May 2019 (2019-05-22), pages 323 - 332, XP085721790, DOI: 10.1016/j.porgcoat.2019.05.029 *
NAGAPPAN, S. ET AL.: "Highly Transparent, Hydrophobic Fluorinated Polymethyl-siloxane/Silica Organic-Inorganic Hybrids for Anti-Stain Coating", MACROMOLECULAR RESEARCH, vol. 21, no. 6, June 2013 (2013-06-01), pages 669 - 680, XP055762953 *
SANGERMANO, M. ET AL.: "Hybrid organic-inorganic coatings based on thiol-ene systems", REACTIVE & FUNCTIONAL POLYMERS, vol. 69, 2009, pages 719 - 723, XP026375344 *
SIRIVIRIYANUN, A. ET AL.: "Anti-fingerprint properties of non-fluorinated organosiloxane self-assembled monolayer-coated glass surfaces", CHEMICAL ENGINEERING JOURNAL, vol. 246, 2014, pages 254 - 259, XP055762955 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114736614A (zh) * 2022-05-11 2022-07-12 深圳市创新精细玻璃有限公司 一种环保型oca光学胶及其制备方法
CN114736614B (zh) * 2022-05-11 2023-11-14 深圳市创新精细玻璃有限公司 一种环保型oca光学胶及其制备方法

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