Classifications

• • 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
  • 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
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/14—Methyl esters, e.g. methyl (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
  • C08F220/12—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
  • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (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
  • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
• • 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
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/10—Esters
  • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
  • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• • 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
  • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
• • 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
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
  • C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
• • 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
  • C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
  • C09D143/02—Homopolymers or copolymers of monomers containing phosphorus
• • 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
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/08—Anti-corrosive paints
• • 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
  • C09D5/16—Antifouling paints; Underwater paints
• • 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
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
  • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

• the present invention relates to a fluorine-containing copolymer and a surface-modified substrate using the same. More particularly, it relates to a fluorine-containing copolymer capable of providing a surface-modified film having excellent water/oil repellency, rust resistance, etc., and a surface-modified base material using the same.
• the applicant of the present application has previously proposed a fluoropolymer comprising a copolymer of a polyfluoroalkyl alcohol (meth)acrylic acid derivative having a perfluoroalkyl group of C 6 or less, which is said to have low bioaccumulation, and this as an active ingredient.
• a polyfunctional monomer such as ethylene glycol di(meth)acrylate may be copolymerized in the fluorine-containing polymer at a ratio of 10% by weight or less. 1, when 2.33% by weight of ethylene glycol dimethacrylate was copolymerized, the reaction product became a gel and was not obtained as a copolymer solution.
• the present invention provides a fluorine-containing copolymer that can be obtained as a copolymer solution and can provide a surface-modified film having excellent water and oil repellency, rust resistance, etc., and surface modification using the same. It is to provide a base material.
• the second object of the present invention is achieved by a surface-modified substrate having a surface-modified film formed from a coating composition comprising such a fluorine-containing copolymer and its solvent.
• the fluorine-containing copolymer of the present invention in which polyfunctional (meth)acrylic acid ester is an essential copolymerization unit and the copolymerization ratio is 2% by weight or less in the copolymer, forms a uniform coating composition together with its solvent. form.
• the surface-modified film formed on the substrate with this coating composition is excellent in water and oil repellency, rust prevention, suppression of rust spreading from scratches, and moisture resistance.
• the antirust agent containing the fluorine-containing polymer consisting of [I], [II] and [III] as an active ingredient is also described in Patent Document 2, but it is also described in Examples 1 to Comparative Example 3 below.
• the water and oil repellency and the ability to suppress the spread of rust from scratches are further improved.
• polyfluoroalkyl alcohol (meth)acrylic acid derivative [I] which is the component (A)
• the following compounds can be exemplified as described in Patent Document 3. and their corresponding methacrylic acid derivatives
• a polyfluoroalkyl alcohol (meth)acrylic acid derivative can be used by itself as one of the fluorine-containing polymerizable monomers. It can also be used in combination with other fluorine-containing polymerizable monomers within the range of about 30% by weight or less based on the total amount.
• R Hydrogen atom, methyl group
• R4 C1 - C6 linear / branched alkylene group
• R5 C1 - C4 lower alkyl group
• Rf C1 - C6 perfluoroalkyl group m : 0 or 1 and the following polyfluoroalkyl group-containing (meth)acrylate monomers are used.
• the fluorine atom-free polymerizable monomer to be copolymerized with the polyfluoroalkyl alcohol (meth)acrylic acid derivative [I] or another fluorine-containing polymerizable monomer [V] the general formula [II ], [III] and [IV] are used.
• Examples of the (meth)acrylic acid ester represented by the general formula [II] as the component (B) include methyl, ethyl, propyl, isopropyl, n-butyl, n-hexyl, 2-ethylhexyl, n-octyl, and lauryl. , an alkyl group such as stearyl, a cycloalkyl group such as cyclohexyl, or an aralkyl group such as benzyl.
• R 1 of component (B) may contain an oxygen atom.
• the (meth)acrylic acid ester represented by the general formula [III] as the component (C) includes, in addition to (meth)acrylic acid, for example, 2-(meth)acryloyloxymethyl acid phosphate, 2-(meth)acryloyl (Meth)acrylates having a phosphoric acid group such as oxyethyl acid phosphate and 2-(meth)acryloyloxyethyl acid phosphate are used.
• R 2 of component (C) may contain an oxygen atom.
• component (D) examples include ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,4-butanediol di(meth) ) acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, tripropylene glycol di( Meth)acrylate, polypropylene glycol di(meth)acrylate, bisphenol A/ethylene oxide adduct diacrylate, dimethyloltricyclodecane diacrylate, glycerin methacrylate acrylate, 3-acryloyloxyglycerin monomethacrylate and the like are used.
• R 3 of component (D) may contain an oxygen atom.
• These functional group-containing (meth)acrylic acid esters contain component (B) in an amount of about 1 to 50% by weight, preferably about 10 to 40% by weight, and component (C) in an amount of about 0.01 to 5% by weight in the fluorine-containing copolymer. % by weight, preferably about 0.1 to 2% by weight, and about 0.01 to 2% by weight, preferably about 0.1 to 2% by weight of component (D). If the amount of component (D) exceeds this range, the copolymerization reaction product will gel.
• the initiator used in a proportion of about 0.1 to 4% by weight, preferably about 0.5 to 2% by weight, based on the total amount of comonomers includes diacyl peroxide, peroxycarbonate, peroxyester and the like. Specifically, isobutyryl peroxide, lauroyl peroxide, stearoyl peroxide, succinic acid peroxide, bis(heptafluorobutyryl)peroxide, pentafluorobutyroylperoxide, bis(4-tert-butylcyclohexyl)peroxide Organic peroxides such as carbonate, di-n-propylperoxydicarbonate and diisopropylperoxydicarbonate are used, and depending on the polymerization method, azo compounds, inorganic peroxides or their redox systems are also used. Depending on the reaction conditions and composition ratio, the polymerization reaction may be difficult to proceed. In such cases, the polymerization initiator may be added and used
• a chain transfer agent can also be used as necessary.
• the copolymerization reaction is carried out at a reaction temperature of about 0 to 100°C, preferably about 5 to 70°C, particularly preferably about 40 to 70°C, using these reaction solvents, reaction initiators, and the like. After completion of the reaction, a copolymer solution having a solid concentration of about 5 to 30% by weight is obtained, and the solvent is removed from this reaction mixture to obtain a fluorine-containing copolymer.
• the polyfluoroalkyl alcohol (meth)acrylic acid derivative copolymer [I] used in the copolymerization reaction was almost completely copolymerized as a result of gas chromatography analysis of unreacted residual comonomers. was confirmed.
• the method for producing a copolymer of polyfluoroalkyl alcohol (meth)acrylic acid derivative is not limited to such a solution polymerization method.
• a method, an emulsion polymerization method, etc. are also used.
• the copolymer of polyfluoroalkyl alcohol (meth)acrylic acid derivative obtained in this way is separated by a method of evaporating to dryness, a method of adding a coagulant such as an inorganic salt to coagulate, etc., and washed with a solvent or the like. It is purified by the method of The weight average molecular weight Mw of the obtained copolymer is shown by high performance liquid chromatography, and the value is about 2,000 to 20,000,000.
• the polymer solution obtained by the solution polymerization method is further added with a fluorinated organic solvent such as 1,4-bis(trifluoromethyl)benzene and 1,3-bis(trifluoromethyl)benzene, preferably used in the polymerization reaction. It is diluted with the same organic solvent as above to a solid content concentration of about 0.01 to 30% by weight, preferably about 0.05 to 5% by weight to form a coating composition, which is used as a surface modifier.
• a fluorinated organic solvent such as 1,4-bis(trifluoromethyl)benzene and 1,3-bis(trifluoromethyl)benzene
• Polymers obtained by water-based emulsion polymerization, suspension polymerization, etc. can be used as they are, or after being diluted with water to a solid content concentration of about 0.1 to 10% by weight, as an aqueous dispersion, or as a coagulant in the polymerization reaction solution. is added to coagulate the polymer, and the copolymer separated by washing with water or an organic solvent is dispersed in water or dissolved in a fluorinated organic solvent to prepare an aqueous dispersion or an organic solvent solution.
• the aqueous dispersion one containing 20% or less of a surfactant and a water-soluble organic solvent is preferably used.
• Such aqueous dispersions or organic solvent solutions can be used, for example, as surface modifiers such as water and oil repellents and oil barriers.
• a coating composition comprising an aqueous dispersion of this copolymer or a solution of these in a fluorinated organic solvent may contain other additives such as a melamine resin, a urea resin, a cross-linking agent such as a blocked isocyanate, a polymer extender, and a silicone.
• additives such as a melamine resin, a urea resin, a cross-linking agent such as a blocked isocyanate, a polymer extender, and a silicone.
• Additives necessary for surface modifier applications such as other water repellent agents such as resins, oils, waxes, insect repellents, antistatic agents, dye stabilizers, anti-wrinkle agents and stain blockers can be added.
• the surface modifier thus obtained is applied to a base material such as metal, paper, film, fiber, cloth, woven fabric, carpet, or fabric products made of filament, fiber, thread, etc., water and oil repellent, It is effectively applied as a rust inhibitor and the like.
• coating, dipping, spraying, padding, roll coating, or a combination of these methods is generally used.
• the material to be treated is padded in this pad bath, then excess liquid is removed with a squeezing roll, dried, and the amount of polymer attached to the material to be treated is about 0.01 to 10% by weight, forming a surface-modified film. form.
• it is generally dried at a temperature of about 100 to 200° C. for about 1 minute to about 2 hours to complete water and oil repellent treatment, rust prevention treatment, and the like.
• a water- and oil-repellent substrate, an antirust substrate, an antirust/coating substrate, etc. having a surface treatment film formed from the coating composition are formed.
• MMA methyl methacrylate
• MAA methacrylic acid
• EGDMA ethylene glycol dimethacrylate
• AIBN azobisisobutyronitrile
• Example 2 In Example 1, the amount of EGDMA was changed to 1.6 g (1.97% by weight), and it was confirmed that the conversion of all comonomers was 99% or more and the copolymerization reaction was carried out.
• Example 3 In Example 1, 10.1 g (12.62% by weight) of benzyl methacrylate (BzMA) was used instead of MMA, and it was confirmed that the conversion of all comonomers was 99% or more and the copolymerization reaction was carried out.
• BzMA benzyl methacrylate
• Example 5 In Example 1, 0.38 g (0.48% by weight) of 2 -methacryloyloxyethyl acid phosphate (Kyoeisha Chemical Products P - 1M) was used instead of MAA, and the amount of C4F9OC2H5 was changed to 112.5 g, and 1 , The amount of 3-bis(trifluoromethyl)benzene was changed to 48.2g, and 40.2g of isopropyl alcohol (IPA) was used, and the conversion of all comonomers was 99% or more, and the copolymerization reaction was carried out. It was confirmed.
• IPA isopropyl alcohol
• Comparative example 1 In Example 1, the amount of EGDMA was changed to 1.9 g (2.33% by weight), but after 21 hours gelation occurred in the reaction vessel and no copolymer solution was obtained.
• Comparative example 2 In Example 1, no MAA was used. It was confirmed that the conversion rate of all comonomers was 99% or more, indicating that the copolymerization reaction was carried out.
• Comparative example 4 In Example 1, no MAA and EGDMA were used. It was confirmed that the conversion rate of all comonomers was 99% or more and the copolymerization reaction was carried out.
• Examples 1 to 5 had high water and oil repellency.
• the copolymers of Examples 1 to 5 have very low falling angles with respect to water and n-hexadecane and excellent liquid removability compared to the copolymers obtained in Comparative Examples 2 to 4. was confirmed.
• Rust prevention evaluation was performed by a salt spray test (JIS Z 2371). A 70 ⁇ 150 ⁇ 1.0 mm aluminum, copper or SPCC test piece was used as the base material, and C 4 F 9 OC 2 H 5 of each fluorine-containing copolymer and 1,3-bis(trifluoromethyl)benzene The test piece was surface-treated by immersing it in the mixed solution (7:3 v/v). The obtained coated test piece was treated as unprocessed. In addition, when the coating film of the non-processed test piece was scratched with a cutter in two diagonal directions of the test piece, it was regarded as cross-cut.
• Example 5 inhibited the spread of rust from scratches as compared with the copolymers obtained in Comparative Examples 2-4.
• Moisture resistance evaluation Moisture resistance was evaluated by moisture permeability (cup method, JIS Z 0208). A film was formed on a polyimide film, and the obtained film was peeled off to obtain an evaluation sample. The permeability (g/m 2 ⁇ 24H) of Example 1 was 190.

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