WO2015141899A1 - Composition liquide de revêtement dur et vitrage en polycarbonate l'utilisant - Google Patents

Composition liquide de revêtement dur et vitrage en polycarbonate l'utilisant Download PDF

Info

Publication number
WO2015141899A1
WO2015141899A1 PCT/KR2014/005997 KR2014005997W WO2015141899A1 WO 2015141899 A1 WO2015141899 A1 WO 2015141899A1 KR 2014005997 W KR2014005997 W KR 2014005997W WO 2015141899 A1 WO2015141899 A1 WO 2015141899A1
Authority
WO
WIPO (PCT)
Prior art keywords
hard coating
liquid composition
coating liquid
formula
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2014/005997
Other languages
English (en)
Korean (ko)
Inventor
우창수
하리모토유키나리
문형랑
이우진
장승우
전환승
한동일
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Samsung SDI Co Ltd
Original Assignee
Samsung SDI Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Samsung SDI Co Ltd filed Critical Samsung SDI Co Ltd
Publication of WO2015141899A1 publication Critical patent/WO2015141899A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/50—Phosphorus bound to carbon only
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • 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
    • C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
    • 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
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes
    • C08J2383/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2483/04—Polysiloxanes
    • C08J2483/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the present invention relates to a hard coating liquid composition and polycarbonate glazing using the same. More specifically, the present invention relates to a novel hard coating solution composition for forming a hard coating layer, and a polycarbonate glazing excellent in wear resistance, reliability (interlayer adhesion) and weather resistance prepared using the same, and a method of manufacturing the same.
  • plastic materials have contributed to the weight reduction of automobiles, improving design and design freedom, granting new functions, and reducing costs. It is preferred as an alternative material for parts that have been difficult to resinize.
  • plastic materials such as polycarbonate (PC) and polymethyl methacrylate (PMMA), have excellent impact resistance, transparency and formability, and are currently used in various automotive parts such as B-pillars, headlamps and sunroofs, and the like. It is used for the manufacture of parts.
  • the plastic material can impart various advantages and uses in areas such as styling / design, weight reduction, stability / safety, etc. of automotive window modules.
  • plastic materials can increase overall design and shape complexity, not only to differentiate the vehicle from competing vehicles, but also to reduce the complexity of the window assembly to automakers by integrating functional components into molded plastic modules.
  • the plastic window module can increase the overall stability of the vehicle by strengthening the occupant's support in a rollover accident.
  • the compound used in the hard coating composition (abrasion resistant coating agent) for forming the hard coating layer includes an acrylic polymer, urethane polymer, epoxy polymer, silicon polymer, silica compound and the like.
  • the conventional hard coating liquid composition increases the wear resistance of the hard coating layer as the crosslinking density increases, but may cause cracks during bending or transportation due to shrinkage of the coating layer, and may reduce adhesion to the plastic substrate. This poor adhesion to the substrate results in shortening the reliability of the glazing system. Therefore, there is a need for the development of a hard coating liquid composition capable of simultaneously improving the wear resistance and reliability (adhesive force) of the polycarbonate glazing (hard coating layer).
  • An object of the present invention is to provide a hard coating liquid composition capable of producing a polycarbonate glazing excellent in wear resistance and reliability (interlayer adhesion), a polycarbonate glazing using the same and a method for producing the same.
  • Another object of the present invention is to provide a hard coating liquid composition capable of forming a hard coating layer having excellent weather resistance, a polycarbonate glazing using the same, and a method of manufacturing the same.
  • the hard coating solution composition is a binder comprising a polymer of a compound represented by the formula (1), and a monomer mixture comprising a compound represented by the formula (2); Phosphorus catalysts; And an inorganic filler;
  • R 1 is an epoxy group or an alkyl group having 1 to 12 carbon atoms containing glycidoxy group
  • R 2 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms
  • R 3 is a substituted or unsubstituted carbon number
  • R 4 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms
  • R 5 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • the amount of the compound represented by Formula 1 may be about 0.5 to about 99.5 mol% of the total monomer mixture, and the amount of the compound represented by Formula 2 may be about 0.5 to about 99.5 mol% of the total monomer mixture. have.
  • the monomer mixture may further include a compound represented by the following Formula 3:
  • R 6 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms
  • R 7 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms
  • c is 0, 2 or 3.
  • the weight average molecular weight of the polymer may be about 800 to about 30,000 g / mol.
  • the phosphorus catalyst may include a compound represented by Formula 4 below:
  • R 8 , R 9 and R 10 are each independently a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms.
  • the inorganic filler may include a nonmetal or a metal oxide.
  • the amount of the phosphorus-based catalyst compound is about 0.01 to about 25 parts by weight based on about 100 parts by weight of the binder, and the content of the inorganic filler is about 1 to about 300 parts by weight based on about 100 parts by weight of the binder. It may be wealth.
  • the hard coating solution composition may further include a solvent.
  • the hard coating liquid composition may further include one or more of a UV absorber, an activity reducing agent, a hindered amine light stabilizer, an antioxidant, and a leveling agent.
  • the polycarbonate glazing is based on a polycarbonate; And a hard coating layer formed on at least one surface of the substrate, wherein the hard coating layer is a cured product of the hard coating liquid composition.
  • the thickness of the polycarbonate substrate is about 1 to about 50 mm, the thickness of the hard coating layer may be about 0.1 to about 20 ⁇ m.
  • the polycarbonate glazing may have a structure in which a primer layer is further formed between the polycarbonate substrate and the hard coating layer.
  • the polycarbonate glazing has a haze difference ( ⁇ Haze) between about 1 and about after wear after about 500 wears under a CS-10F wear wheel and about 500 g load conditions using a Taber abraser. 6 may be.
  • Another aspect of the invention relates to a method for producing a polycarbonate glazing.
  • the manufacturing method is characterized in that it comprises the step of applying the hard coating solution composition on at least one side of the polycarbonate substrate, and then curing to form a hard coating layer.
  • the manufacturing method includes forming a primer layer on at least one side of the polycarbonate substrate; After applying the hard coating liquid composition on the surface of the primer layer, it may include the step of curing to form a hard coating layer.
  • the present invention has the effect of providing a hard coating liquid composition capable of producing a polycarbonate glazing excellent in wear resistance, reliability (interlayer adhesion), weather resistance, and the like, a polycarbonate glazing using the same, and a method of manufacturing the same.
  • FIG. 1 is a cross-sectional view of a polycarbonate glazing according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view of a polycarbonate glazing according to another embodiment of the present invention.
  • the hard coating solution composition according to the present invention can form a hard coating layer such as plastic glazing, and includes a binder, a phosphorus catalyst, and an inorganic filler.
  • the binder used in the present invention includes a siloxane polymer including an epoxy group and a siloxane bond (-Si-O-Si-), wherein the polymer is represented by the following Chemical Formula 1, and Chemical Formula 2 It is characterized in that the polymer of the monomer mixture containing the compound.
  • R 1 represents an epoxy group or an alkyl group having 1 to 12 carbon atoms containing glycidoxy group, for example, a glycidoxypropyl group, a glycidyl group, and an epoxycyclohexyl group
  • R 2 and R 4 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, for example, a hydrogen atom, a methyl group, an ethyl group, a propyl group, isopropyl group, a butyl group, an isobutyl group, tert-butyl group and the like
  • R 3 and R 5 are each independently substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, for example methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert -Butyl group etc .
  • substituted means that the hydrogen atom is a halogen group, an alkyl group of 1 to 10 carbon atoms, a haloalkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 12 carbon atoms, a heteroaryl group of 6 to 12 carbon atoms, carbon atoms It means what was substituted by substituents, such as an alkoxy group of 1-20, these combinations.
  • examples of the compound represented by Formula 1 include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-gly Cidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 5,6-epoxyhexyltrier Methoxysilane, 3-glycidoxypropyldimethylethoxysilane, 3-glycidoxypropyldimethylmethoxysilane, mixtures thereof and the like can be exemplified, but is not limited thereto.
  • examples of the compound represented by Formula 2 include methyltrimethoxysilane, methyltriethoxysilane, trimethoxysilane, triethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n -Propyltrimethoxysilane, n-propyltriethoxysilane, n-butyltrimethoxysilane, n-butyltriethoxysilane, isobutyltrimethoxysilane, isobutyltriethoxysilane, tert-butyltrimethoxy Silane, tert-butyltriethoxysilane, mixtures thereof, and the like can be exemplified, but is not limited thereto.
  • the content of the compound represented by Formula 1 may be about 0.5 to about 99.5 mol%, for example about 1 to about 80 mol%, specifically about 2 to about 50 mol% of the total monomer mixture
  • the content of the compound represented by Formula 2 may be about 0.5 to about 99.5 mol%, for example about 20 to about 99 mol%, specifically about 50 to about 98 mol%, of the total monomer mixture. It may be excellent in the wear resistance of the hard coating layer (glazing) in the above range.
  • the monomer mixture may further include a compound represented by Formula 3 below.
  • R 6 represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, for example, a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and tert-butyl
  • R 7 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, etc.
  • c is 0, 2 or 3.
  • the content of the compound represented by Formula 3 is about 0 to about 10 moles, for example about 0.1 to about 7 moles, specifically about about 100 moles of the total of the compounds of Formulas 1 and 2 0.5 to about 5 molar parts. Wear resistance of the hard coating layer (glazing) in the above range can be more excellent, and the occurrence of cracks can be reduced.
  • the polymer may be prepared by a known production method.
  • the monomer mixture may be prepared by condensation reaction, and, if necessary, may be condensation reaction after hydrolysis of each monomer. Such condensation reactions, hydrolysis and the like can be easily carried out by those skilled in the art.
  • the monomer mixture may be hydrolyzed and condensed in the presence of water and acetic acid (catalyst) as in the following Preparation Examples.
  • the polymer may be branched, ladder, network structure, mixed structure thereof, and the like, and the weight average molecular weight measured by gel permeation chromatography (GPC) is about 800 to about 30,000 g / mol, for example about 1,000 to about 10,000 g / mol.
  • GPC gel permeation chromatography
  • the coating property of the hard coating solution composition may be excellent in the above range, and the wear resistance, reliability, etc. of the hard coating layer may be excellent.
  • the binder is used for ordinary binders such as epoxy resins, amide resins, acrylic resins, urethane resins, silicone resins, copolymers thereof, etc. in addition to the siloxane polymers. It may further include a resin.
  • a resin for a binder other than the siloxane polymer the content thereof may be about 0.1 to about 100 parts by weight based on about 100 parts by weight of the siloxane polymer, but is not limited thereto.
  • the binder may be used in a state (solution) in which solid content such as the polymer is dissolved in a solvent, but is not limited thereto.
  • a solvent any solvent capable of dissolving the binder without reactivity with the binder (solid content) may be used without limitation.
  • the solvent include alcohols having 1 to 15 carbon atoms, hydrocarbon solvents such as aliphatic hydrocarbons, alicyclic hydrocarbons and aromatic hydrocarbons, ethers such as halogenated hydrocarbon solvents, aliphatic ethers and alicyclic ethers, and mixtures thereof. have.
  • the content of the solvent is not limited as long as it can dissolve binder solids such as polymer, but may be, for example, about 0 to about 900 parts by weight based on about 100 parts by weight of the binder solids.
  • the phosphorus catalyst used in the present invention may include a compound represented by the following Chemical Formula 4 as a curing catalyst for forming a hard coating layer.
  • R 8 , R 9 and R 10 are each independently a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms.
  • a substituted or unsubstituted cyclic alkyl group having 5 to 20 carbon atoms which may or may not contain a hetero atom such as a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, an oxygen atom (O), or a nitrogen atom (N).
  • the phosphorus based catalyst may include, but is not limited to, triphenylphosphine, tri (p-tolyl) phosphine, triisopropylphosphine, mixtures thereof, and the like.
  • the content of the phosphorus-based catalyst compound may be about 0.01 to about 25 parts by weight, for example about 1 to about 10 parts by weight, based on about 100 parts by weight of the binder (based on solids). It may be excellent in the degree of curing at the time of forming the hard coating layer in the above range.
  • the inorganic filler used for this invention can improve the abrasion resistance of a hard coat layer
  • the inorganic filler (particle) used for the normal hard coat liquid composition can be used.
  • nonmetals or metal oxides such as silicon oxide, aluminum oxide, cerium oxide, zirconium oxide, zinc oxide, titanium oxide, and mixtures thereof may be used, but are not limited thereto.
  • the inorganic filler is 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, Silane coupling agents such as 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane and 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane It may be surface treated (coated) with a surface treatment material, but is not limited thereto.
  • silica sicon oxide
  • titanium oxide, zinc oxide, etc. which were surface-treated with silane coupling agents, such as 3-glycidoxy propyl trimethoxysilane, can be used.
  • the inorganic filler may have an average particle diameter (D50) of about 1 to about 100 nm, for example, about 2 to about 50 nm. Within this range, wear resistance and the like can be improved without deteriorating other physical properties of the hard coat layer.
  • D50 average particle diameter
  • the surface-treated inorganic filler may be a form in which at least a portion of the inorganic filler is coated with a surface treatment material, for example, a form in which a hydroxyl group on the surface of the inorganic filler and a functional group such as an epoxy group of the surface treatment material are combined.
  • a surface treatment material for example, a form in which a hydroxyl group on the surface of the inorganic filler and a functional group such as an epoxy group of the surface treatment material are combined.
  • the content of the surface treatment material may be about 1 to about 50 parts by weight based on about 100 parts by weight of the inorganic filler, but is not limited thereto.
  • the content of the inorganic filler may be about 1 to about 300 parts by weight, for example about 10 to about 115 parts by weight, based on about 100 parts by weight of the binder (based on solids). It is possible to manufacture a hard coating layer having good adhesion to the lower film quality in the above range while having excellent wear resistance.
  • the hard coating solution composition of the present invention may further include a solvent.
  • the solvent may be used as long as it is a solvent that can dissolve the binder without being reactive with the binder and can evaporate when the hard coat layer is formed.
  • the solvent may be selected in consideration of the solubility of the binder, the evaporation rate of the solvent, and the like, and a plurality of solvents may be mixed and used.
  • the solvent may be the same as or different from the solvent of the solution binder.
  • the solvent may include hydrocarbons such as alcohols having 1 to 15 carbon atoms, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, ethers such as halogenated hydrocarbon solvents, aliphatic ethers, alicyclic ethers, and the like.
  • hydrocarbons such as alcohols having 1 to 15 carbon atoms, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, ethers such as halogenated hydrocarbon solvents, aliphatic ethers, alicyclic ethers, and the like.
  • alcohol solvents such as methanol, ethanol, propanol, butanol, ethylene glycol, diacetone alcohol, hydrocarbon solvents such as pentane, hexane, cyclohexane, toluene, xylene, halogen hydrocarbon solvents such as methylene chloride and trichloroethane, Ethers such as dibutyl ether, dioxane, tetrahydrofuran and propylene glycol methyl ether and the like can be used.
  • hydrocarbon solvents such as pentane, hexane, cyclohexane, toluene, xylene, halogen hydrocarbon solvents such as methylene chloride and trichloroethane
  • Ethers such as dibutyl ether, dioxane, tetrahydrofuran and propylene glycol methyl ether and the like can be used.
  • the content of the solvent is not particularly limited as long as it can dissolve the binder and evaporate after applying the hard coating solution.
  • about 100 parts by weight of the binder (based on solids) may be about 100 to about 2,000 parts by weight, but is not limited thereto.
  • the hard coating liquid composition of the present invention is an additive used in a conventional hard coating liquid composition, for example, ultraviolet (UV) absorber, Hindered Amine Light Stabilizer (HALS), activity reducing agent (quencher), antioxidant It may further include an additive including a leveling agent, a curing agent, a mixture thereof, and the like.
  • UV absorbers, HALS, deactivating agents, antioxidants, etc. may be added to further improve the weatherability of the hard coating layer
  • leveling agents may be added to improve the coating properties or slip properties of the coating, etc.
  • the curing agent may be added to further increase the degree of curing of the coating layer to improve wear resistance or scratch resistance.
  • additive 2,4-dihydroxybenzophenone, 2,3,4-trihydroxybenzophenone, Tinuvin-400 (BASF), Tinuvin-479 (BASF), Tinuvin 99-2 (BASF), ADK STAB 1413 ( Adeka), LA-31 (Adeka), 4,6-dibenzoyl resorcinol, Tinuvin-123 (BASF), Tinuvin-292 (BASF), Tinuvin-152 (BASF), Tinuvin-5151 (BASF) , hydroquinone, methoxyhydroquinone, Irganox 245 (BASF Corporation), Irganox 1098 (BASF Corporation), Irganox 1135 (BASF Corporation), Irganox 3114 (BASF Corporation), Irgafos 168 (BASF Corporation), and the like, but are not limited thereto. Do not.
  • the content of the additive may be about 0.01 to about 80 parts by weight based on about 100 parts by weight of the binder (based on solids), but is not limited thereto.
  • the hard coating liquid composition of the present invention may be prepared by, for example, (A) simply mixing and stirring the components, or (B) polymerizing the monomer mixture in the presence of the inorganic filler to prepare a mixture of a binder and an inorganic filler. And it can manufacture by mixing and stirring remaining components, such as a phosphorus catalyst here.
  • the production method (B) As compared with the production method (A), it is possible to obtain a hard coating liquid composition in which the inorganic filler is more uniformly dispersed in the binder matrix, whereby the interaction with the binder is strong even in the hard coating layer. Inorganic filler dispersion with high uniformity can be obtained.
  • the polycarbonate glazing 100 includes a polycarbonate substrate 110 and a hard coating layer 120 formed on at least one surface of the substrate 110.
  • the hard coating layer 120 is a cured product of the hard coating liquid composition.
  • the polycarbonate substrate 110 used in the present invention may include a conventional polycarbonate resin.
  • a conventional polycarbonate resin for example, polycarbonates, polycarbonate copolymers or polycarbonate blending resins can be used.
  • the blending resin include polymer resins such as polyamide, thermoplastic polyurethane (TPU), acrylonitrile-styrene-acrylonitrile, polymethylmethacrylate, polyester, acrylonitrile-butadiene-styrene, and mixtures thereof.
  • Blended polycarbonate may be used, but is not limited thereto.
  • the polycarbonate is reacted with a dihydric phenolic compound and phosgene in the presence of a molecular weight modifier and a catalyst according to a conventional manufacturing method, or esterification reaction of a dihydric phenolic compound with a carbonate precursor such as diphenylcarbonate and And / or via transesterification.
  • a bisphenol compound may be used as the dihydric phenol compound, and for example, 2,2-bis (4-hydroxyphenyl) propane (“bisphenol A”) may be used. Can be used.
  • the bisphenol A may be partially or wholly replaced by another type of dihydric phenol compound.
  • the polycarbonate-based resin in view of the safety and transparency required as a substrate for polycarbonate glazing, has a tensile strength of about 60 MPa or more, a tensile modulus of about 1.5 GPa or more, a Vicat softening point of about 120 ° C. or more, total
  • the light transmittance may be about 80% or more, but is not limited thereto.
  • the thickness of the polycarbonate substrate 110 may be about 1 to about 50 mm, for example about 1 to about 10 mm. It may be excellent in mechanical strength, solubility, transparency and the like as the glazing substrate in the above range.
  • the hard coating layer 120 used in the present invention is a cured after applying the hard coating liquid composition.
  • Curing of the hard coating liquid composition may be performed by a conventional curing method using heat and / or ultraviolet rays, and upon curing, crosslinking occurs in a binder matrix containing an inorganic filler, thereby increasing the degree of curing and forming a network structure.
  • the hard coating layer 120 may be formed of a single layer structure or a laminated structure of two or more layers.
  • the hard coating layer 120 may have a thickness of about 0.1 ⁇ m to about 20 ⁇ m, for example, about 1 ⁇ m to about 10 ⁇ m.
  • the polycarbonate glazing 100 may be excellent in abrasion resistance, scratch resistance, and the like, and may have excellent adhesion to the substrate 110 to obtain reliability.
  • Figure 2 shows a cross-sectional view of a polycarbonate glazing according to another embodiment of the present invention.
  • the polycarbonate glazing 100 according to the present invention may have a structure in which a primer layer 130 is further formed between the polycarbonate substrate 110 and the hard coating layer 120.
  • the primer layer 130 used in the present invention plays a role of coupling (coupling) and stress relaxation, crack prevention, etc., between the substrate 110 and the hard coating layer 120, and improves long-term reliability. Can help.
  • the primer layer 130 may be a primer layer used for conventional polycarbonate glazing, and may be formed by a method such as curing after primer coating or film insert molding, but is not limited thereto.
  • the primer layer 130 may be formed from a conventional primer layer forming material (primer).
  • the primer layer forming material may include, for example, at least one of an organopolysiloxane resin, an acrylic resin, an epoxy resin, a polyester resin, a polyurethane resin, a copolymer resin thereof, and a blending resin thereof.
  • the present invention is not limited thereto.
  • copolymer resins such as an epoxy resin, an acrylic resin, and a urethane-acrylate resin, etc. can be used.
  • the resin may be included in the primer layer forming material in the form of a monomer.
  • it may be included in the form of an acrylate monomer as in Preparation Example 5 below.
  • the primer layer 130 may have a stacked structure having different or the same forming materials for the purpose of improving interlayer bonding strength.
  • the primer layer forming material and manufacturing method are well known to those skilled in the art.
  • the primer layer 130 may be formed from a primer layer forming material (primer) including a binder and a phosphorus catalyst used in the hard coating solution composition of the present invention.
  • primer layer forming material may further include an inorganic filler, an additive, and / or a solvent used in the hard coating liquid composition of the present invention, but is not limited thereto. That is, in another embodiment of the present invention, the primer layer 130 may be part of the laminated structure hard coating layer 120 with the same or different interlayer components.
  • the binder used in the primer layer is about 0.5 to about 99.5 mol%, for example about 10 to about 70 mol%, specifically about 20 to about 60 mole%, and about 0.5 to about 99.5 mole%, for example about 30 to about 90 mole%, specifically about 40 to about 80 mole% of a compound represented by Formula 2 It may be a polymer. It may be excellent in the wear resistance of the hard coating layer (glazing) in the above range.
  • the content of the phosphorus-based catalyst compound is about 0.01 to about 25 parts by weight, for example about 0.1 to about 15 parts by weight, specifically about 1 to about 10 parts by weight, based on about 100 parts by weight of the binder (based on solids).
  • the inorganic filler may be excellent in the degree of curing at the time of forming the hard coating layer in the above range.
  • the content of the inorganic filler is about 300 parts by weight or less, for example, about 0.01 to about 115 parts by weight, based on about 100 parts by weight of the binder (based on solids).
  • Parts by weight specifically about 10 to about 100 parts by weight, and the content of the additive is about 0.01 to about 80 parts by weight, for example about 1 to about 80 parts by weight, based on about 100 parts by weight of the binder (based on solids)
  • the amount of the solvent may be about 100 to about 2,000 parts by weight, for example about 150 to about 900 parts by weight, based on about 100 parts by weight of the binder (based on solids).
  • the binder and the compounding components of the primer may be well dissolved or dispersed, and the coating may be excellent because the evaporation is easily performed after the primer is applied.
  • the primer layer 130 may have a thickness of about 0.1 ⁇ m to about 20 ⁇ m, for example, about 0.5 ⁇ m to about 10 ⁇ m.
  • the adhesion between the substrate 110 and the hard coating layer 120 in the above range can be excellent in reliability, and may be more effective in abrasion resistance, stress relaxation, crack prevention, and the like.
  • the polycarbonate glazing 100 of the present invention may be manufactured by applying the hard coating liquid composition to at least one surface of the polycarbonate substrate 110 and curing the hard coating layer 120 to form the hard coating layer 120.
  • Application of the hard coating solution composition may be by a coating method such as bar coating, roll coating, spin coating, dip coating, flow coating, spray coating, or the like.
  • a coating method such as bar coating, roll coating, spin coating, dip coating, flow coating, spray coating, or the like.
  • the present invention is not limited thereto.
  • the curing may be thermal curing or ultraviolet curing, UV curing is advantageous for the small size, but as the size of the molding is recently increased, the tendency to adopt the thermosetting method is increasing.
  • the curing can be thermal curing at a temperature of about 100 to about 140 ° C., such as about 110 to about 130 ° C., for example, for about 1 to about 180 minutes. It is possible to form a hard coating layer having excellent wear resistance in the temperature range.
  • the polycarbonate glazing 100 forms a primer layer 130 on at least one surface of the polycarbonate substrate 110, and after curing the hard coating liquid composition on the surface of the primer layer 130, It may be manufactured by forming the hard coating layer 120.
  • the formation of the hard coat layer 120 may be performed in the same manner as in the embodiment.
  • the primer layer 130 may be formed by a conventional primer layer forming method, for example, coating a primer layer forming material (primer) or molding a film insert, followed by curing.
  • Application of the primer may be by conventional coating methods such as bar coating, roll coating, spin coating, dip coating, flow coating, spray coating, and the like. have.
  • the curing may be performed at about 80 to about 150 °C for about 1 to about 180 minutes, but is not limited thereto.
  • the polycarbonate glazing according to the present invention has a haze difference ( ⁇ Haze) before and after abrasion when worn about 500 times under a CS-10F wear wheel and a load of about 500 g using a taper abraser.
  • ⁇ Haze haze difference
  • a ⁇ Transmittance may be about -0.1 to about 0.1.
  • the wear resistance of the polycarbonate glazing may be excellent in the above range.
  • the plastic glazing of the present invention has excellent adhesion between the substrate and the hard coating layer, and has excellent wear resistance, scratch resistance, reliability, weather resistance, and the like, and thus is suitable for automotive glazing, in particular, for vehicle windows.
  • colloidal silica (trade name: Ludox R TMA, manufactured by Sigma-Aldrich), 23.82 g of glycidoxypropyltrimethoxysilane (manufactured by Sigma-Aldrich) as a coupling agent (surface treatment agent), 263.32 g of isopropyl alcohol as a solvent was added to a three-neck 1L jacketed reactor equipped with a reflux system, and then stirred at 25 ° C. for 1 hour. Thereafter, the mixture was heated to 65 ° C, refluxed for 3 hours, cooled to room temperature, and a surface-treated inorganic filler (solid content: 27.3 wt%, solvent: 72.7 wt%) was prepared.
  • a primer layer forming material (primer 2) was prepared in the same manner as in Preparation Example 1, except that the inorganic filler (C) was not used.
  • a urethane acrylate resin (UNIDIC RC27-947, DIC CORPORATION), 200 parts by weight of isopropyl alcohol, 25 parts by weight of 2,4-dihydroxybenzophenone as a UV absorber, followed by stirring 2 parts by weight of a photoinitiator (Irgacure 184, BASF Co., Ltd.) and stirred at room temperature for 1 hour to prepare a primer layer forming material (primer 4).
  • a photoinitiator Irgacure 184, BASF Co., Ltd.
  • DPHA dipentaerythritol hexaacrylate
  • PETA pentaerythritol triacrylate
  • MCS methoxyethanol
  • Primer 4 a primer layer forming material was prepared.
  • IPA isopropyl alcohol
  • BYK306, BASF polyether-modified polydimethyl siloxane
  • hard coating liquid 1 100 parts by weight of the binder (A1), 5 parts by weight of the triphenylphosphine (B1), 80 parts by weight of the inorganic filler (C), 37 parts by weight of isopropyl alcohol, and 2,4-dihydroxybenzo as an ultraviolet absorber After mixing 3 parts by weight of phenone (2,4-dihydroxybenzophenone), the mixture was stirred at room temperature for 1 hour to prepare a hard coating liquid composition (hard coating liquid 1).
  • a hard coating solution composition (hard coating solution 2) was prepared in the same manner as in Example 1, except that tri (p-tolyl) phosphine (B2) was used instead of triphenylphosphine (B1).
  • a hard coating liquid composition (hard coating liquid 3) was prepared in the same manner as in Example 1, except that the ultraviolet absorbent (triphenylphosphine (B1)) was not used.
  • a hard coating liquid composition (hard coating liquid 4) was prepared in the same manner as in Example 1.
  • a hard coating solution composition (hard coating solution 5) was prepared in the same manner as in Example 1.
  • hard coating solution 6 The same method as in Example 1, except that binder (A2) was used instead of the binder (A1) and tri (p-tolyl) phosphine (B2) was used instead of the triphenylphosphine (B1).
  • binder (A2) was used instead of the binder (A1)
  • tri (p-tolyl) phosphine (B2) was used instead of the triphenylphosphine (B1).
  • hard coating solution 6 hard coating solution 6
  • a binder 100 parts by weight of an epoxy resin (NC-3000, Nippon Kayaku Co., Ltd.), 5 parts by weight of the triphenylphosphine (B1), 60 parts by weight of a curing agent (HE100C-10, Air Water), 160 parts by weight of isopropyl alcohol After mixing 3 parts by weight of 2,4-dihydroxybenzophenone (2,4-dihydroxybenzophenone) as an ultraviolet absorber, the mixture was stirred at room temperature for 1 hour to prepare a hard coating solution composition (hard coating solution 9).
  • an epoxy resin NC-3000, Nippon Kayaku Co., Ltd.
  • a curing agent H100C-10, Air Water
  • isopropyl alcohol 160 parts by weight of isopropyl alcohol
  • a hard coating solution composition (hard coating solution 10) was prepared in the same manner as in Comparative Example 1, except that tri (p-tolyl) phosphine (B2) was used instead of triphenylphosphine (B1).
  • a hard coating liquid composition (hard coating liquid 11) was prepared in the same manner as in Comparative Example 1, except that the ultraviolet absorbent (triphenylphosphine (B1)) was not used.
  • a binder 100 parts by weight of a urethane acrylate resin (UNIDIC RC27-947, DIC CORPORATION) and 250 parts by weight of isopropyl alcohol were mixed and stirred, and then 2 parts by weight of a photoinitiator (Irgacure 184, BASF Co., Ltd.) was added thereto, and at room temperature for 1 hour. Stirred. Next, 80 parts by weight of silica particle resin (PL-1-IPA, FUSO Co., Ltd.) as an inorganic filler, and 3 parts by weight of 2,4-dihydroxybenzophenone (2,4-dihydroxybenzophenone) as a UV absorber are mixed to form a hard coating solution. (Hard Coating Solution 12) was prepared.
  • DPHA dipentaerythritol hexaacrylate
  • PETA pentaerythritol triacrylate
  • MCS 2-methoxyethanol
  • Igacure 184 Igacure as a photoinitiator. 184, BASF Co., Ltd.
  • IPA isopropyl alcohol
  • BYK306, BASF polyether-modified polydimethylsiloxane
  • Hard coating solution 13 80 parts by weight of silica particle resin (PL-1-IPA, FUSO Co., Ltd.) as an inorganic filler, and 3 parts by weight of 2,4-dihydroxybenzophenone (2,4-dihydroxybenzophenone) as a UV absorber were mixed to obtain a hard coating solution composition ( Hard coating solution 13) was prepared.
  • silica particle resin PL-1-IPA, FUSO Co., Ltd.
  • 2,4-dihydroxybenzophenone 2,4-dihydroxybenzophenone
  • a hard coating liquid composition (Examples 1 to 6, and Comparative Examples 1 to 5) on one side of a polycarbonate substrate (product name: LEXAN, manufacturer: GE Corporation) having a size of 30 cm ⁇ 20 cm ⁇ 3 mm, respectively was applied using a mayer bar.
  • Examples 1 to 6 and Comparative Examples 1 to 3 of the hard coating liquid composition was leveled at room temperature for 20 minutes, and then placed in an oven and thermoset at 130 ° C. for 1 hour to form a hard coating layer having a thickness of 5 ⁇ m.
  • the hard coating liquid compositions of Examples 4 and 5 were leveled at room temperature for 20 minutes, and then irradiated with 350 mJ / cm light with a high pressure mercury lamp to form a hard coating layer having a thickness of 5 ⁇ m. According to the following physical property measurement method, after measuring the physical properties of the produced polycarbonate glazing, the results are shown in Tables 1, 2 and 3.
  • a primer layer forming material of Preparation Examples 1 to 5 may be prepared on one surface of a polycarbonate substrate (product name: LEXAN, manufacturer: GE Corporation) having a size of 30 cm ⁇ 20 cm ⁇ 3 mm. It was applied using.
  • a polycarbonate substrate product name: LEXAN, manufacturer: GE Corporation
  • the primer layer forming materials of Preparation Examples 1 to 3 after leveling (leveling) at room temperature for 20 minutes, it was put in an oven at 130 ° C. and thermosetted for 30 minutes to form a primer layer having a thickness of 3 ⁇ m.
  • the primer layer forming material of 5 after leveling at room temperature for 20 minutes, and irradiated with 350 mJ / cm light with a high pressure mercury lamp to form a primer layer having a thickness of 3 ⁇ m.
  • the hard coating solution composition was applied to one surface of the primer layer, and a hard coating layer having a thickness of 5 ⁇ m was formed in the same manner as in Examples 9 to 16 and Comparative Examples 6 to 10. .
  • the results are shown in Tables 1, 2 and 3.
  • Thickness measurement (unit: ⁇ m): The thickness of the prepared hard coating layer and the primer layer was measured using F-20 (device name) equipment of Filmetrics. After measuring five times, the average value is indicated.
  • Example 1 Example Primer layer forming material Hard Coating Liquid Composition Wear resistance Adhesion Water bath Weather resistance Permeability Difference Haze differences Exterior Adhesion Exterior YI difference 9 - Example 1 0.0 2.8 100/100 OK 100/100 OK 0.8 10 - Example 2 0.0 2.7 100/100 OK 100/100 OK 0.8 11 - Example 3 0.0 2.6 100/100 OK 100/100 OK 3.4 12 - Example 4 0.0 4.8 100/100 OK 100/100 OK 0.9 13 - Example 5 0.0 2.5 100/100 OK 100/100 OK 0.7 14 - Example 6 0.0 2.4 100/100 OK 100/100 OK 0.7 15 Preparation Example 1 Example 1 0.0 3.5 100/100 OK 100/100 OK 0.3 16 Preparation Example 1 Example 3 0.0 3.5 100/100 OK 100/100 OK 0.6 17 Preparation Example 1 Example 4 0.0 4.9 100/100 OK 100/100 OK 0.3 18 Preparation Example 2 Example 1 0.0 3.6 100/100 OK 100/100 OK 0.3 19 Preparation Example 3 Example 1 0.0
  • Example 3 0.0 2.9 100/100 OK 100/100 OK 0.5 28 Preparation Example 2
  • Example 3 0.0 2.9 100/100 OK 100/100 OK 0.5 29
  • Preparation Example 3 0.0 3.4 100/100 OK 100/100 OK 0.6
  • Preparation Example 4 Example 3 0.0 3.8 100/100 OK 100/100 OK 0.6 31
  • Preparation Example 5 Example 3 0.0 3.8 100/100 OK 100/100 OK 0.6
  • Preparation Example 1 Example 4 0.0 2.7 100/100 OK 100/100 OK 0.5 33
  • Example 3 0.0 3.1 100/100 OK 100/100 OK 0.6 35
  • Preparation Example 4 Example 4 0.0 3.7 100/100 OK 100/100 OK 0.7 36
  • Preparation Example 5 Example 4 0.0 3.8 100/
  • the polycarbonate glazing of the present invention is excellent in abrasion resistance, adhesion, water bath test results (adhesion in harsh conditions), weather resistance and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention concerne une composition liquide de revêtement dur contenant : un liant comprenant un polymère d'un mélange de monomères comprenant un composé représenté par la formule chimique 1 et un composé représenté par la formule chimique 2 ; un catalyseur à base de phosphore ; et une charge inorganique. Un vitrage en polycarbonate, pourvu d'une couche de revêtement dur formée à l'aide de la composition liquide de revêtement dur, présente d'excellentes propriétés de résistance à l'usure, fiabilité (adhérence intercouche) et résistance aux intempéries.
PCT/KR2014/005997 2014-03-19 2014-07-04 Composition liquide de revêtement dur et vitrage en polycarbonate l'utilisant Ceased WO2015141899A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020140032381A KR20150109221A (ko) 2014-03-19 2014-03-19 하드코팅액 조성물　및 이를 이용한 폴리카보네이트 글레이징
KR10-2014-0032381 2014-03-19

Publications (1)

Publication Number Publication Date
WO2015141899A1 true WO2015141899A1 (fr) 2015-09-24

Family

ID=54144844

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/005997 Ceased WO2015141899A1 (fr) 2014-03-19 2014-07-04 Composition liquide de revêtement dur et vitrage en polycarbonate l'utilisant

Country Status (2)

Country Link
KR (1) KR20150109221A (fr)
WO (1) WO2015141899A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11027312B2 (en) * 2016-12-15 2021-06-08 Covestro Deutschland Ag Transparently coated polycarbonate component, its production and use

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102664602B1 (ko) * 2023-08-14 2024-05-10 광주과학기술원 폴리카보네이트 기반 광학 적층체, 그 제조 방법 및 이를 이용한 커버윈도우

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070044477A (ko) * 2004-08-02 2007-04-27 엑사테크 엘.엘.씨. 자동차용 플라스틱 글레이징을 위한 장식용 잉크 시스템
KR20070058076A (ko) * 2005-12-01 2007-06-07 주식회사 삼양사 내스크래치성 및 가공성이 우수한 폴리카보네이트 글레이징
KR20110128933A (ko) * 2009-03-18 2011-11-30 바스프 에스이 개질된 실리카 입자 및 이를 포함하는 방오성 중합체 조성물
KR20130063506A (ko) * 2010-05-10 2013-06-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 열 흡수성 및 개선된 염색성을 갖는 폴리머 조성물
KR20130078601A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 플라스틱 글레이징 및 그 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070044477A (ko) * 2004-08-02 2007-04-27 엑사테크 엘.엘.씨. 자동차용 플라스틱 글레이징을 위한 장식용 잉크 시스템
KR20070058076A (ko) * 2005-12-01 2007-06-07 주식회사 삼양사 내스크래치성 및 가공성이 우수한 폴리카보네이트 글레이징
KR20110128933A (ko) * 2009-03-18 2011-11-30 바스프 에스이 개질된 실리카 입자 및 이를 포함하는 방오성 중합체 조성물
KR20130063506A (ko) * 2010-05-10 2013-06-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 열 흡수성 및 개선된 염색성을 갖는 폴리머 조성물
KR20130078601A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 플라스틱 글레이징 및 그 제조방법

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11027312B2 (en) * 2016-12-15 2021-06-08 Covestro Deutschland Ag Transparently coated polycarbonate component, its production and use

Also Published As

Publication number Publication date
KR20150109221A (ko) 2015-10-01

Similar Documents

Publication Publication Date Title
WO2020149597A1 (fr) Stratifié optique
WO2019093731A1 (fr) Composition photodurcissable et couche de revêtement comprenant le produit durci associé
WO2017209413A1 (fr) Polyamide-imide transparent haute résistance et son procédé de préparation
WO2013187699A1 (fr) Composition de résine de revêtement dur de siloxane
WO2012008780A2 (fr) Composition de revêtement antiréfléchissant et antireflet, film antiréfléchissant et antireflet, et procédé de fabrication de celui-ci
WO2014123308A1 (fr) Plaque de polarisation et afficheur à cristaux liquides comportant cette plaque de polarisation
WO2015009114A1 (fr) Vitrage en polycarbonate et son procédé de production
WO2017171489A1 (fr) Procédé de fabrication d'un film d'isolation
WO2019240408A1 (fr) Oligomère de siloxane ayant un métal organique, procédé de préparation d'oligomère de siloxane, composition de revêtement dur contenant un oligomère de siloxane, film de revêtement dur et dispositif d'affichage
WO2017039159A1 (fr) Composition durcissant à basse température, film durci formé dessus, et dispositif électronique présentant le film durci
WO2018110830A2 (fr) Film de fenêtre, son procédé de fabrication et dispositif d'affichage l'intégrant
JP2010285507A (ja) 接着性硬化性組成物
WO2018159918A1 (fr) Substrat de fenêtre de couverture et dispositif d'affichage d'image comprenant celui-ci
WO2020013461A1 (fr) Oligomère de siloxane comprenant un métal organique, procédé de production d'oligomère de siloxane, composition de revêtement dur comprenant l'oligomère de siloxane, film de revêtement dur et dispositif d'affichage
WO2015141899A1 (fr) Composition liquide de revêtement dur et vitrage en polycarbonate l'utilisant
JP2002235005A (ja) 光学用材料用組成物、光学用材料およびその製造方法
WO2022108053A1 (fr) Fenêtre de recouvrement pour dispositif d'affichage flexible et dispositif d'affichage flexible
WO2023054866A1 (fr) Film optique ayant une structure multicouche et dispositif d'affichage le comprenant
WO2021194317A1 (fr) Film optique ayant une excellente résistance aux chocs et dispositif d'affichage le comprenant
WO2017078488A1 (fr) Composition adhésive optique et film adhésif optique
WO2016108676A1 (fr) Composition de résine pour revêtement dur, et film de revêtement dur comprenant une forme durcie de cette dernière en tant que couche de revêtement
KR101768294B1 (ko) 실록산계 수지 및 이를 포함하는 코팅액 조성물
WO2012002706A2 (fr) Film protecteur
WO2021002671A1 (fr) Film de revêtement destiné à être fixé à la surface extérieure d'un pare-brise d'automobile et son procédé de préparation
WO2020091321A1 (fr) Stratifié à revêtement dur

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14886663

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14886663

Country of ref document: EP

Kind code of ref document: A1