WO2023286725A1 - Absorbeur d'uv et son procédé de fabrication, composition, corps moulé et film de revêtement - Google Patents

Absorbeur d'uv et son procédé de fabrication, composition, corps moulé et film de revêtement Download PDF

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WO2023286725A1
WO2023286725A1 PCT/JP2022/027201 JP2022027201W WO2023286725A1 WO 2023286725 A1 WO2023286725 A1 WO 2023286725A1 JP 2022027201 W JP2022027201 W JP 2022027201W WO 2023286725 A1 WO2023286725 A1 WO 2023286725A1
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group
carbon atoms
resin
parts
ultraviolet
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PCT/JP2022/027201
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English (en)
Japanese (ja)
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優美香 千葉
僚一 辰巳
大輔 槇
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東洋インキＳｃホールディングス株式会社
トーヨーカラー株式会社
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Priority to CN202280048114.6A priority Critical patent/CN117651750A/zh
Priority to KR1020237044600A priority patent/KR20240033216A/ko
Publication of WO2023286725A1 publication Critical patent/WO2023286725A1/fr

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    • 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
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B17/00—Azine dyes
    • C09B17/04—Azine dyes of the naphthalene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • 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

Definitions

  • the present invention relates to an ultraviolet absorber, its manufacturing method, composition, molded article, and coating film.
  • UV absorbers are added to resins to impart UV absorbency to moldings and coatings.
  • UV absorbers not only ultraviolet light with a wavelength of less than 400 nm, but also light in the visible short wavelength range of about 400 to 420 nm, damages organic matter and the human body. It is pointed out to give Therefore, for specific applications, there is a demand for an ultraviolet absorber capable of absorbing light in the short wavelength region of visible light.
  • an ultraviolet absorber to an optical film such as a polarizing plate protective film to prevent discoloration of these optical films.
  • an ultraviolet absorber is added to the antireflection film in order to prevent deterioration of the near-infrared absorber contained in the antireflection film due to ultraviolet rays.
  • various organic substances such as fluorescent materials and phosphorescent materials are used in the light-emitting elements of organic EL displays.
  • An ultraviolet absorber is added to the coating film on the surface.
  • UV absorbers that absorb UV light and light in the visible light short wavelength region of about 400 to 420 nm for the purpose of protecting organic substances in materials.
  • molded articles and coating films for the above applications have been required to further improve high ultraviolet shielding properties, heat resistance and light resistance, and are less likely to be colored and deteriorated due to heating or exposure to ultraviolet rays over a long period of time. Those that retain excellent visible transparency and UV shielding properties are desired.
  • Patent Documents 1 and 2 disclose a benzotriazole-based UV absorber that absorbs visible light in the short wavelength region of about 400 to 420 nm.
  • JP 2018-177696 A Japanese Patent Publication No. 2016-514756
  • UV absorbers absorb light in the short wavelength region of visible light of about 400 to 420 nm, they have low heat resistance and light resistance, and UV absorption decreases due to heating or exposure to UV rays over a long period of time. I had a problem. In addition, there is a problem that the transparency of the coating film and the molded article is lowered when the amount of the ultraviolet absorber added is increased in order to obtain sufficient ultraviolet shielding properties.
  • One embodiment of the present invention has heat resistance, light resistance, and transparency in addition to excellent ultraviolet absorption that absorbs not only ultraviolet rays of less than 400 nm but also light in the visible light short wavelength region of about 400 to 420 nm.
  • the object is to provide an ultraviolet absorber.
  • the embodiment of the present invention is as follows.
  • One or more ultraviolet absorbing dyes selected from the group consisting of compounds represented by the following general formulas (1) to (3), and one selected from the group consisting of Na, Mg, Al, K, Ca, and Fe
  • R 1b to R 1g , R 2a to R 2g , and R 3a to R 3g each independently represent a hydrogen atom, a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, represents any one selected from the group consisting of an iodine atom, a nitrile group, a nitro group, a sulfo group, R 7 , Ar 1 , and groups represented by general formulas (4-1) to (4-3) below.
  • R 7 is any selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and an alkenyloxy group having 1 to 20 carbon atoms. represents a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitrile group, a nitro group, a carboxyl group, or a sulfo group.
  • alkenyl groups 1 to 20 alkenyl groups, alkoxy groups having 1 to 20 carbon atoms, and alkenyloxy groups having 1 to 20 carbon atoms, and one or more -O-, -CO-, -COO between carbon atoms -, -OCO-, -CONH-, or -NHCO- may be linked.
  • Ar 1 represents any one selected from the group consisting of an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and a biphenyl group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, a carbon alkenyl group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, alkenyloxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, fluorine atom, chlorine It may have substituents of atoms, bromine atoms, iodine atoms, nitrile groups, nitro groups, carboxyl groups, or sulfo groups.
  • R 4 , R 5 and R 6 each independently represent any one selected from the group consisting of a hydroxyl group, R 7 and Ar 1 .
  • X 1 represents any selected from the group consisting of -CO-, -COO-, -OCO-, -CONH-, and -NHCO-
  • R 8 is hydrogen represents any one selected from the group consisting of an atom, a hydroxyl group, R7 and Ar1 .
  • * in general formula (4-1) represents a bonding site with the naphthalene ring of general formulas (1) to (3).
  • X 2 and X 3 are each independently selected from the group consisting of -CO-, -COO-, -OCO-, -CONH- and -NHCO-
  • R 9 represents an arylene group having 6 to 20 carbon atoms
  • R 10 represents R 7 or Ar 1 .
  • * in general formula (4-2) represents a bonding site with the naphthalene ring of general formulas (1) to (3).
  • X 4 and X 5 are each independently selected from the group consisting of -CO-, -COO-, -OCO-, -CONH- and -NHCO- wherein R 11 represents a linear or branched alkylene group having 1 to 20 carbon atoms or an arylene group having 6 to 20 carbon atoms, R 12 represents R 7 or Ar 1 , and n is 1 to is 20.
  • * in general formula (4-3) represents a bonding site with the naphthalene ring of general formulas (1) to (3).
  • ⁇ 4> The UV absorber according to any one of ⁇ 1> to ⁇ 3>, and a triazine ring-containing compound and a benzotriazole ring-containing compound that are compounds other than the compounds represented by general formulas (1) to (3) , and at least one second UV absorber selected from the group consisting of benzophenone ring-containing compounds.
  • ⁇ 5> A composition comprising the ultraviolet absorber according to any one of ⁇ 1> to ⁇ 3> and a coloring material that blocks light in the visible wavelength range of 450 to 650 nm.
  • composition according to ⁇ 5> wherein the colorant contains two or more chromatic colorants.
  • the ultraviolet absorber according to any one of ⁇ 1> to ⁇ 3>, and one selected from the group consisting of phthalocyanine compounds, naphthalocyanine compounds, squarylium compounds, cyanine compounds, and diketopyrrolopyrroles
  • a composition comprising the above near-infrared absorbent, wherein the near-infrared absorbent has a maximum absorption in a wavelength range of 600 to 1500 nm.
  • a composition comprising the UV absorber according to any one of ⁇ 1> to ⁇ 3> and a resin.
  • a composition comprising the ultraviolet absorber according to any one of ⁇ 1> to ⁇ 3>, a photopolymerizable compound, and a photopolymerization initiator.
  • ⁇ 11> A molded article molded from the composition according to any one of ⁇ 4> to ⁇ 10>.
  • ⁇ 12> A coating film formed from the composition according to any one of ⁇ 4> to ⁇ 10>.
  • ⁇ 13> The method for producing an ultraviolet absorber according to any one of ⁇ 1> to ⁇ 3>, wherein a poor solvent containing water is added to the reaction solution for synthesizing the ultraviolet absorbing dye to separate the liquid, and the metal
  • a step of removing the components a step of washing the UV-absorbing dye with alcohol, water, or a mixture thereof after the liquid separation and filtration; washing the UV-absorbing dye by reslurrying the UV-absorbing dye in alcohol, water, or a mixture thereof. and one or more steps selected from the group consisting of the steps of reslurrying and washing the UV-absorbing dye with an acid solution, thereby reducing the content of the metal component contained in the UV-absorbing dye.
  • a method for producing an ultraviolet absorber A method for producing an ultraviolet absorber.
  • an ultraviolet absorber in addition to excellent ultraviolet absorption that absorbs not only ultraviolet rays of less than 400 nm but also light in the visible short wavelength region of about 400 to 420 nm, it has heat resistance, light resistance, and transparency.
  • An ultraviolet absorber, a composition using the same, a molded article, and a coating film can be provided.
  • FIG. 1 is an example of a diffraction pattern by powder X-ray diffraction of an ultraviolet absorber of one embodiment of the present invention.
  • the ultraviolet absorber of one embodiment of the present invention is one or more ultraviolet absorbing dyes selected from the compounds represented by the following general formulas (1) to (3) (hereinafter also referred to as “ultraviolet absorbing dye (A)"). , and a metal component containing one or more metal atoms selected from the group consisting of Na, Mg, Al, K, Ca, and Fe (hereinafter also referred to as “metal component (B)”), and a metal component ( The content of B) is 0.1 to 50000 ppm with respect to the ultraviolet absorber.
  • R 1b to R 1g , R 2a to R 2g , and R 3a to R 3g each independently represent a hydrogen atom, a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. It represents any one selected from the group consisting of atoms, nitrile groups, nitro groups, sulfo groups, R 7 , Ar 1 , and groups represented by the following general formulas (4-1) to (4-3).
  • R 7 is any selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and an alkenyloxy group having 1 to 20 carbon atoms. represents a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitrile group, a nitro group, a carboxyl group, or a sulfo group.
  • alkenyl groups 1 to 20 alkenyl groups, alkoxy groups having 1 to 20 carbon atoms, and alkenyloxy groups having 1 to 20 carbon atoms, and one or more -O-, -CO-, -COO between carbon atoms -, -OCO-, -CONH-, or -NHCO- may be linked.
  • Ar 1 represents any one selected from the group consisting of an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and a biphenyl group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, a carbon alkenyl group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, alkenyloxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, fluorine atom, chlorine It may have substituents of atoms, bromine atoms, iodine atoms, nitrile groups, nitro groups, carboxyl groups, or sulfo groups.
  • R 4 , R 5 and R 6 each independently represent any one selected from the group consisting of a hydroxyl group, R 7 and Ar 1 .
  • X 1 represents any selected from the group consisting of -CO-, -COO-, -OCO-, -CONH-, and -NHCO-
  • R 8 is hydrogen represents any one selected from the group consisting of an atom, a hydroxyl group, R7 and Ar1 .
  • * in general formula (4-1) represents a bonding site with the naphthalene ring of general formulas (1) to (3).
  • X 2 and X 3 are each independently selected from the group consisting of -CO-, -COO-, -OCO-, -CONH- and -NHCO-
  • R 9 represents an arylene group having 6 to 20 carbon atoms
  • R 10 represents R 7 or Ar 1 .
  • * in general formula (4-2) represents a bonding site with the naphthalene ring of general formulas (1) to (3).
  • X 4 and X 5 are each independently selected from the group consisting of -CO-, -COO-, -OCO-, -CONH- and -NHCO- wherein R 11 represents a linear or branched alkylene group having 1 to 20 carbon atoms or an arylene group having 6 to 20 carbon atoms, R 12 represents R 7 or Ar 1 , and n is 1 to is 20.
  • * in general formula (4-3) represents a bonding site with the naphthalene ring of general formulas (1) to (3).
  • the ultraviolet absorber of the embodiment of the present invention is a light in the visible light short wavelength region of about 400 to 420 nm in addition to the ultraviolet region of less than 400 nm due to the action of the ultraviolet absorbing dye (A) having a naphthalene ring bonded to the triazine ring. can be absorbed.
  • the ultraviolet absorber contains an appropriate amount of a metal component (B) containing one or more metal atoms selected from the group consisting of Na, Mg, Al, K, Ca, and Fe. It has an unexpectedly remarkable effect of ensuring light resistance, heat resistance, and ultraviolet absorption.
  • the ultraviolet absorbing dye (A) can absorb wavelengths, so the amount of the ultraviolet absorbing dye (A) added can be suppressed, suppressing the deterioration of the transparency of the molded article and the coating film, and has the effect of improving transparency.
  • the mechanism by which such an effect is obtained is speculated as follows. That is, since the ultraviolet absorbing dye (A) contained in the ultraviolet absorber of the embodiment of the present invention contains a triazine ring moiety having a lone pair in its molecular structure, the ultraviolet absorbing dye (A) and the metal atom to form a complex, and metal ions are easily incorporated into the dye skeleton. As a result, it is assumed that the crystallinity of the ultraviolet-absorbing dye is improved, the deterioration due to heating and light irradiation is less likely to occur, and the heat resistance and light resistance are improved.
  • the ultraviolet absorbing dye incorporates too many metal ions, the amount of the ultraviolet absorbing dye component is reduced, and it is thought that the ultraviolet absorbability is reduced.
  • the amount By setting the amount to 0.1 to 50000 ppm (more preferably 0.1 to 10000 ppm or 0.1 to 1000 ppm), an appropriate amount of metal ions can be incorporated into the dye skeleton, so that excellent ultraviolet rays can be obtained. Absorbency can be maintained.
  • the ultraviolet absorbing dye (A) is selected from one or more compounds represented by formulas (1) to (3), and may be used alone or in combination.
  • the compounds represented by formulas (1) to (3) absorb light in the visible short wavelength region of about 400 to 420 nm in addition to the ultraviolet region of less than 400 nm.
  • the compound of general formula (1) can absorb the longest wavelengths, and is most preferable from the viewpoint of absorbing light of longer wavelengths. mentioned.
  • general formula (3) has the shortest maximum absorption wavelength among general formulas (1) to (3), but is most preferable from the viewpoint of being nearly colorless.
  • Examples include compounds represented by the following formulas.
  • general formula (2) is preferable from the viewpoint of being able to balance the absorption of light with longer wavelengths and the fact that it is nearly colorless, and examples thereof include compounds represented by the following formula.
  • the ultraviolet absorber contains an ultraviolet absorbing dye (A), and further contains 0.1 to 50000 ppm of a metal component (B) per 100 parts by mass of the ultraviolet absorber.
  • A ultraviolet absorbing dye
  • B metal component
  • the compounds represented by general formulas (1) to (3) contained in the ultraviolet absorbing dye (A) can be synthesized using known methods for synthesizing compounds having a triazine structure.
  • a synthesis method of the general formula (1) for example, there is a method of addition reaction of cyanuric chloride with naphthol using aluminum trichloride.
  • a synthesis method of general formula (2) for example, a method of addition reaction of 2,4-dichloro-6-phenyl-1,3,5-triazine with naphthol using aluminum trichloride can be mentioned.
  • a method of addition reaction of 2-chloro-4,6-diphenyl-1,3,5-triazine with naphthol using aluminum trichloride can be mentioned.
  • methyl 2-hydroxy-1-naphthoate and benzamidine hydrochloride may be condensed and cyclized using sodium methoxide, but these synthesis methods are typical production methods. It is described and is not limited to this.
  • the metal component (B) contained in the ultraviolet absorber contains one or more metal atoms selected from the group consisting of Na, Mg, Al, K, Ca and Fe.
  • the metal atoms can be often used as an acid catalyst used in the synthesis method, so the content of the metal component (B) can be controlled by controlling the Al amount by the purification method after synthesis. Further, depending on the method for synthesizing the ultraviolet absorbing dye (A), the above metal atoms may not be contained at all. It is also good to control the content of Various methods are known for measuring metal atoms.
  • the content of the metal component (B) can be easily determined by, for example, diluting a solution obtained by adding nitric acid to an ultraviolet absorber and decomposing it with microwaves to an appropriate concentration and using inductively coupled plasma emission spectrometry (ICP). can do.
  • the content of the metal component (B) is preferably 0.1 to 50000 ppm, more preferably 0.1 to 10000 ppm, even more preferably 0.1 to 1000 ppm, and even if it is 1 to 48200 ppm, relative to the ultraviolet absorber. good.
  • the content of the metal component (B) means the total content of ions of Na, Mg, Al, K, Ca, and Fe.
  • a poor solvent such as methanol containing water is added to the reaction solution for synthesizing the UV-absorbing dye (A).
  • a method of separating liquids and removing metal components A method of washing by sprinkling alcohol such as methanol or water, or a mixture thereof, on the wet cake (compound concentrated by the step of removing metal components) after liquid separation and filtration; A method of reslurrying the wet cake in alcohol such as methanol or water, or a mixed solution thereof for washing; provided, but not limited to.
  • the ultraviolet absorber has diffraction peaks at least at Bragg angles 2 ⁇ ( ⁇ 0.3°) of 7.6° and 13.2° in the X-ray diffraction pattern of the compound represented by the general formula (1) with CuK ⁇ rays.
  • the ratio of these diffraction peaks is 1:1.3 to 1:0.7
  • the X-ray diffraction pattern of the compound represented by the general formula (2) with CuK ⁇ rays shows that at least the Bragg angle 2 ⁇ ( ⁇ 0.3°) has diffraction peaks at 8.0° and 14.5°, and the ratio of these diffraction peaks (XRD ratio) is 1:1.3 to 1:0.7.
  • the crystallinity there is a risk that the particles will grow large due to the strong turbidity, and the transparency of the molded article and coating film will be reduced.
  • the ratio is 1:1.4 or more, the crystallinity is low and the particles are fine, but the cohesive force is strong, so there is a possibility that the transparency of the molded article and coating film may be lowered.
  • the crystallinity and the cohesive force can be appropriately balanced, and the transparency of the molded article and coating film can be further improved.
  • a method for measuring the powder X-ray diffraction spectrum and a method for calculating the diffraction peak intensity ratio will be described later.
  • the ultraviolet absorber of the embodiment of the present invention can be dissolved or present as particles in the composition.
  • the particles preferably have an average primary particle diameter of about 5 nm to 100 ⁇ m, more preferably about 10 nm to 10 ⁇ m, and even more preferably about 20 nm to 500 nm.
  • the ultraviolet absorber can suppress deterioration in transparency by having particles with an appropriate average primary particle size.
  • the average primary particle diameter can be obtained by arithmetically averaging the major diameters of about 20 primary particles in a magnified image of 1,000 to 10,000 times using a transmission electron microscope.
  • the UV absorber can be produced, for example, by synthesizing a compound contained in the UV absorbing dye (A) and then adjusting the content of the metal component (B) in the UV absorbing dye (A). , The content of the metal component (B) is reduced by ⁇ method for refining the ultraviolet absorbing dye (A)>, or the content is increased by adding a metal atom separately after synthesizing the ultraviolet absorbing dye (A).
  • the materials necessary for synthesizing the compound contained in the ultraviolet absorbing dye (A) are placed in an Erlenmeyer flask, stirred to obtain a reaction solution, and a poor solvent such as methanol containing water is added little by little to the reaction solution for separation.
  • the metal components are removed by removing the metal components, and the wet cake after the liquid separation and filtration (the compound concentrated by the metal component removal step) is sprinkled with alcohol or water, or a mixture thereof to wash the metal components.
  • a UV absorber with a reduced content of (B) can be produced.
  • the composition of the embodiment of the present invention comprises at least One type of second ultraviolet absorber (hereinafter also referred to as "ultraviolet absorber (C)”) can be contained.
  • second ultraviolet absorber hereinafter also referred to as "ultraviolet absorber (C)
  • the UV-absorbing dye (A) and the UV absorber By combining the above compounds contained in C), it is possible to broaden the ultraviolet region and to easily and effectively shield the short wavelength region of visible light with a wavelength of about 400 to 420 nm.
  • the compounds contained in the ultraviolet absorbing dye (A) and the ultraviolet absorbent (C) protect each other, better light resistance and heat resistance can be obtained.
  • the benzotriazole ring-containing compound is generally a compound that absorbs light with a wavelength of 360 nm or less.
  • TINUVIN P "TINUVIN PS”
  • TINUVIN 109 "TINUVIN 234"
  • TINUVIN 326 "TINUVIN 328”
  • TINUVIN 329 manufactured by BASF Japan.
  • triazine ring-containing compounds other than the compounds represented by the general formulas (1) to (3) are generally compounds that absorb light having a wavelength of 360 nm or less.
  • -[4,6-di(2,4-xylyl)-1,3,5-triazin-2-yl]-5-octyloxyphenol 2-[4,6-bis(2,4-dimethylphenyl) -1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol
  • 2,4-bis(2-hydroxy-4-butoxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazine 2 -[4-[(2-hydroxy-3-(2′-ethoxyphenyl)-1,
  • triazine ring-containing compounds which are compounds other than the compounds represented by formulas (1) to (3), include “KEMISORB 102" manufactured by Chemipro Kasei Co., Ltd., "TINUVIN 400", “TINUVIN 405", and “TINUVIN 405" manufactured by BASF Japan.
  • TINUVIN 460 "TINUVIN 477-DW”, “TINUVIN 479”, “TINUVIN 1577”, “ADEKA STAB LA-46", “ADEKA STAB LA-F70” manufactured by ADEKA Corporation, "CYASORB UV-1164” manufactured by Sun Chemical Co., Ltd., etc. is mentioned.
  • benzophenone ring-containing compounds are generally compounds that absorb light with a wavelength of 360 nm or less, and examples thereof include 2,4-di-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, Sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 2-hydroxy-4-n-octoxybenzophenone, 2,2-di-hydroxy-4-methoxybenzophenone, hexyl 2-(4-diethylamino-2- hydroxybenzoyl)benzoate, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 1,4-bis(4-benzoyl-3-hydroxyphenoxy)butane, 2-hydroxy- 4-octoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2,2',4,4'-tetrahydroxybenzophenone and the like.
  • the content of the ultraviolet absorber (C) is preferably 0.005 to 50% by mass, more preferably 0.01 to 40% by mass, based on the non-volatile content of the composition.
  • the content of the ultraviolet absorber can be designed according to the desired spectral cut rate.
  • the content of the ultraviolet absorber containing the ultraviolet absorbing dye (A) is preferably 0.005 to 50% by mass, more preferably 0.01 to 40% by mass, based on the non-volatile content of the composition.
  • the content of the ultraviolet absorber can be designed according to the desired spectral cut rate.
  • the composition of the embodiment of the present invention can contain a coloring material (hereinafter also referred to as "coloring material (D)”) that blocks 80% or more of the visible wavelength range of 450 to 650 nm. .
  • the colorant (D) preferably contains two or more chromatic colorants. Since the ultraviolet absorber of the embodiment of the present invention strongly absorbs wavelengths of 420 nm or less, it is combined with a chromatic coloring agent that absorbs a specific wavelength range of 450 to 650 nm to cut wavelengths of 700 nm or less. Since light in the infrared region can be used, for example, it can be used as a bandpass material that appropriately adjusts the spectrum depending on the purpose. In addition, since the ultraviolet absorber protects the coloring material (D) from ultraviolet rays, the light resistance and heat resistance of the composition as a whole are improved.
  • coloring material (D) examples include blue pigments, yellow pigments, purple pigments, red pigments, and the like.
  • Organic pigments may be organic pigments, for example, diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, and polyazo, aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavanthrone, anthantrone, and indanthrone.
  • Anthraquinone pigments such as , pyranthrone, or violanthrone, quinacridone pigments, perinone pigments, perylene pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, threne pigments, metal complex pigments etc.
  • Dyes may also be used as organic dyes, and examples thereof include anthraquinone dyes, monoazo dyes, disazo dyes, oxazine dyes, aminoketone dyes, xanthene dyes, quinoline dyes, and triphenylmethane dyes. mentioned. When a dye is used, it is effective to use a polar group of an anionic dye or a cationic dye to incorporate it into the resin and impart solubility in an organic solvent.
  • Blue pigments include, for example, C.I. I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like.
  • C.I means a color index (C.I.; published by The Society of Dyers and Colorists).
  • the blue dye is C.I. I. acid blue 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 13, 14, 15, 17, 19, 21, 22, 23, 24, 25, 26, 27, 29, 34, 35, 37, 40, 41, 41:1, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 62, 62:1, 63, 64, 65, 68, 69, 70, 73, 75, 78, 79, 80, 81, 83, 8485, 86, 88, 89, 90, 90:1, 91, 92, 93, 95, 96, 99, 100, 103, 104, 108, 109, 110, 111, 112, 113, 114, 116, 117, 118, 119, 120, 123, 124, 127, 127: 1, 128, 129, 135, 137, 138, 143, 145, 147, 150, 155, 159, 169, 174, 175, 176,
  • C.I. I. Direct Blue 1, 2, 3, 4, 6, 7, 8, 8:1, 9, 10, 12, 14, 15, 16, 19, 20, 21, 21:1, 22, 23, 25, 27, 29, 31, 35, 36, 37, 40, 42, 45, 48, 49, 50, 53, 54, 55, 58, 60, 61, 64, 65, 67, 79, 96, 97, 98: 1, 101, 106, 107, 108, 109, 111, 116, 122, 123, 124, 128, 129130, 130:1, 132, 136, 138, 140, 145, 146, 149, 152, 153, 154, 156, 158, 158: 1, 164, 165, 166, 167, 168, 169, 170, 174, 177, 181, 184, 185, 188, 190, 192, 193, 206, 207, 209, 213, 215, 225, 226, 229, 230, 231, 242, 243, 244, 253, 254, 260
  • Yellow pigments include, for example, C.I. I. Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95,97,100,101,104,105,108,109,110,111,116,117,119,120,126,127,127:1,128,129,133,134,136,138,139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189,
  • a yellow dye is, for example, C.I. I. Acid yellow 2,3,4,5,6,7,8,9,9:1,10,11,11:1,12,13,14,15,16,17,17:1,18,20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40:1, 41, 42, 42:1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66, 67, 68, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 199 and the like.
  • C.I. Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44:1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, 134 and the like.
  • Purple pigments include, for example, C.I. I. Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
  • a purple dye is, for example, C.I. I. acid violet 1, 2, 3, 4, 5, 5:1, 6, 7, 7:1, 9, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 23, 24, 25, 27, 29, 30, 31, 33, 34, 36, 38, 39, 41, 42, 43, 47, 49, 51, 63, 67, 72, 76, 96, 97, 102, 103, 109, etc. is mentioned.
  • C.I. I. Direct Violet 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 21, 22, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 51, 52, 54, 57, 58, 61, 62, 63, 64, 71, 72, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 93, 97 and the like.
  • Red pigments include, for example, C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53: 3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81: 3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190
  • An orange pigment that acts similarly to a red pigment is, for example, C.I. I. and orange pigments such as Pigment Orange 36, 38, 43, 51, 55, 59, 61, and the like.
  • the red dye is, for example, C.I. I. acid red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 25:1, 26, 26:1, 26:2, 27, 29, 30, 31, 32, 33, 34, 35, 36, 37, 39, 40, 41, 42, 43, 44, 45, 47, 50, 52, 53, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 67, 68, 70, 71, 73, 74, 76, 76: 1, 80, 81, 82, 83, 85, 86, 87, 88, 89, 91, 92, 93, 97, 99, 102, 104, 106, 107, 108, 110, 111, 113, 114, 115, 116, 120, 123, 125, 127, 128, 131, 132, 133, 134, 135, 137, 138, 141, 142, 143, 144, 148
  • Dyes in the coloring material (D) have good spectral characteristics and excellent color development properties, but have problems with light resistance and heat resistance. Therefore, in order to improve these problems, it is preferable to use the basic dye as a salt-forming compound that forms salt using an organic acid and perchloric acid.
  • Organic acids are preferably organic sulfonic acids and organic carboxylic acids. Among them, naphthalenesulfonic acid such as Tobias acid and perchloric acid are preferable in terms of resistance.
  • it is preferable to use it after forming a salt with a resin having an anionic group and it is also preferable to use it as a salt-forming compound that forms a salt together with a resin having a betaine structure and an organic acid.
  • anionic dyes including acid dyes and direct dyes can be used as a salt-forming compound using a compound having a cationic group or a resin having a cationic group as a counter ion to improve heat resistance, light resistance, and solvent resistance.
  • a resin having a cationic group in the synthesis of the salt-forming compound, and it is more preferable to use the resin having a cationic group in its side chain and an organic acid to form a salt.
  • the anionic dye can be preferably used in terms of durability by sulfonamidating it and using it as a sulfonic acid amide compound.
  • the coloring material (D) is a blue pigment and Pigment. Blue. 15:3 or Pigment. Blue. 15:6, Pigment. Yellow. 139, Pigment. Violet. 23 is preferably used. In molding applications, Pigment. Blue. 15:3 or Pigment. Blue. 15:6, Pigment. Yellow. 147, Solvent. Red. 52 is preferably used.
  • the content of the coloring material (D) is preferably 0.005 to 50% by mass, more preferably 0.005 to 20% by mass, even more preferably 0.5 to 50% by mass, based on the non-volatile content of the composition.
  • the content of the ultraviolet absorber can be designed according to the desired spectral cut rate.
  • a dye derivative can be added to the composition of the embodiment of the present invention as necessary.
  • a dye derivative is a compound having an acidic group, a basic group, a neutral group, or the like in an organic dye residue.
  • Dye derivatives include, for example, compounds having an acidic substituent such as a sulfo group, a carboxyl group, and a phosphoric acid group; or compounds having neutral substituents such as phthalimidoalkyl groups.
  • Organic dyes include, for example, diketopyrrolopyrrole-based pigments, anthraquinone-based pigments, quinacridone-based pigments, dioxazine-based pigments, perinone-based pigments, perylene-based pigments, thiazineindigo-based pigments, triazine-based pigments, benzimidazolone-based pigments, benzo Indole pigments such as isoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, azo pigments such as azo, disazo and polyazo. be done.
  • the pigment derivatives can be used alone or in combination of two or more.
  • the composition of the embodiment of the present invention comprises one or more selected from the group consisting of cyanine compounds, phthalocyanine compounds, naphthalocyanine compounds, indigo compounds, immonium compounds, anthraquinone compounds, pyrrolopyrrole compounds, squarylium compounds, and croconium compounds.
  • a near-infrared absorbing agent hereinafter also referred to as "near-infrared absorbing agent (E)
  • the near-infrared absorbing agent (E) has a maximum absorption in the wavelength range of 600 to 1500 nm.
  • the spectrum can be appropriately adjusted, and the ultraviolet absorber of the embodiment of the present invention suppresses deterioration of the near-infrared absorber (E), thereby improving durability.
  • the near-infrared absorber (E) is a compound that has maximum absorption at a wavelength of 600-1500 nm.
  • the maximum absorption is preferably 800-1000 nm.
  • Cyanine compounds WO 2006/006573, WO 2010/073857, JP 2013-241598, JP 2016-113501, JP 2016-113504, etc.; JP-A-4-23868, JP-A-06-192584, JP-A-2000-63691, International Publication No. 2014/208514, etc.; JP, JP 2009-29955 A, International Publication No.
  • the squarylium compound is preferably a compound represented by the following general formula (4).
  • R 1 to R 4 each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, —OR 10 , —COR 11 , —COOR 12 , —OCOR 13 , —NR 14 R 15 , —NHCOR 16 , —CONR 17 R 18 , —NHCONR 19 R 20 , —NHCOOR 21 , —SR 22 , —SO 2 R 23 , —SO 2 OR 24 , -NHSO 2 R 25 , -SO 2 NR 26 R 27 , -B(OR 28 ) 2 and -NHBR 29 R 30 ; each of R 10 to R 30 is independently selected from the group consisting of a hydrogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group,
  • R 24 of —SO 2 OR 24 is a hydrogen atom (ie sulfo group)
  • the hydrogen atom may be dissociated (ie sulfonate group) or in a salt state.
  • R 1 and R 2 , R 3 and R 4 may combine with each other to form a ring.
  • the "substituent” includes, for example, a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, -OR 100 , -COR 101 , -COOR 102 , - OCOR 103 , —NR 104 R 105 , —NHCOR 106 , —CONR 107 R 108 , —NHCONR 109 R 110 , —NHCOOR 111 , —SR 112 , —SO 2 R 113 , —SO 2 OR 114 , —NHSO 2 R 115 , or —SO 2 NR 116 R 117 and the like.
  • R 100 to R 117 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group or an aralkyl group.
  • R 102 of —COOR 102 is hydrogen (ie, carboxyl group)
  • the hydrogen atom may be dissociated (ie, carbonate group), or may be in a salt state.
  • R 114 of —SO 2 OR 114 is a hydrogen atom (ie, sulfo group)
  • the hydrogen atom may be dissociated (ie, sulfonate group) or in a salt state.
  • Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
  • the number of carbon atoms in the alkyl group is preferably 1-20, more preferably 1-12, and particularly preferably 1-8.
  • Alkyl groups may be linear, branched or cyclic.
  • the alkenyl group preferably has 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms.
  • Alkenyl groups may be linear, branched or cyclic.
  • the alkynyl group preferably has 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms.
  • Alkynyl groups may be linear, branched or cyclic.
  • the aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 15 carbon atoms, and particularly preferably 6 to 10 carbon atoms.
  • the alkyl portion of the aralkyl group is the same as the alkyl group described above.
  • the aryl portion of the aralkyl group is the same as the above aryl group.
  • the aralkyl group preferably has 7 to 40 carbon atoms, more preferably 7 to 30 carbon atoms, and particularly preferably 7 to 25 carbon atoms.
  • the heteroaryl group is preferably a single ring or a condensed ring, more preferably a single ring or a condensed ring with 2 to 8 condensed numbers, and particularly preferably a monocyclic ring or a condensed ring with 2 to 4 condensed numbers.
  • the number of heteroatoms constituting the ring of the heteroaryl group is preferably 1-3.
  • a heteroatom constituting the ring of the heteroaryl group is preferably a nitrogen atom, an oxygen atom, or a sulfur atom.
  • a heteroaryl group is preferably a 5- or 6-membered ring.
  • the number of carbon atoms constituting the ring of the heteroaryl group is preferably 3-30, more preferably 3-18, particularly preferably 3-12.
  • Alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, and aralkyl groups may have a substituent or may be unsubstituted. Examples of the substituent include the "substituent" described above.
  • the squarylium compound is more preferably a compound represented by the following general formula (5).
  • R 5 to R 8 each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, —OR 50 , —COR 51 , —COOR 52 , —OCOR 53 , —NR 54 R 55 , —NHCOR 56 , —CONR 57 R 58 , —NHCONR 59 R 60 , —NHCOOR 61 , —SR 62 , —SO 2 R 63 , —SO 2 OR 64 , —NHSO 2 R 65 , —SO 2 NR 66 R 67 , —B(OR 68 ) 2 and —NHBR 69 R 70 .
  • R 50 to R 70 each independently represent a hydrogen atom, an optionally substituted alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group and aralkyl group.
  • R 52 of —COOR 52 is hydrogen (ie, carboxyl group)
  • the hydrogen atom may be dissociated (ie, carbonate group), or it may be in the form of a salt.
  • R 64 of —SO 2 OR 64 is a hydrogen atom (ie, sulfo group)
  • the hydrogen atom may be dissociated (ie, sulfonate group) or in a salt state.
  • R 5 and R 6 and R 7 and R 8 may combine with each other to form a ring.
  • the pyrrolopyrrole compound is preferably a compound represented by the following general formula (6).
  • R 1x and R 1y each independently represent an alkyl group, an aryl group or a heteroaryl group
  • R 2 and R 3 each independently represent a hydrogen atom or a substituent
  • R 2 and R 3 may combine with each other to form a ring
  • R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group
  • R 4 is It may be covalently or coordinately bonded to at least one selected from the group consisting of R 1x , R 1y and R 3
  • R 4x R 4y each independently represents a substituent.
  • General formula (6) is described in JP-A-2009-263614, JP-A-2011-68731, and International Publication No. 2015/166873.
  • R 1x and R 1y are each independently preferably an aryl group or a heteroaryl group, more preferably an aryl group.
  • the alkyl group, aryl group and heteroaryl group represented by R 1x and R 1y may have a substituent or may be unsubstituted.
  • substituents include alkoxy groups, hydroxy groups, halogen atoms, cyano groups, nitro groups, —OCOR 11 , —SOR 12 , —SO 2 R 13 and the like.
  • R 11 to R 13 each independently represent a hydrocarbon group or a heteroaryl group. Examples of substituents include those described in paragraphs 0020 to 0022 of JP-A-2009-263614.
  • substituents are alkoxy groups, hydroxy groups, halogen atoms, cyano groups, nitro groups, -OCOR 11 , -SOR 12 and -SO 2 R 13 .
  • the group represented by R 1x and R 1y is preferably an alkoxy group having a branched alkyl group or an aryl group having a group represented by —OCOR 11 as a substituent.
  • the branched alkyl group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms.
  • At least one of R 2 and R 3 is preferably an electron-withdrawing group, more preferably R 2 represents an electron-withdrawing group and R 3 represents a heteroaryl group.
  • a heteroaryl group is preferably a 5- or 6-membered ring.
  • the heteroaryl group is preferably a single ring or a condensed ring, preferably a single ring or a condensed ring with 2 to 8 condensed numbers, more preferably a monocyclic ring or a condensed ring with 2 to 4 condensed numbers.
  • the number of heteroatoms constituting the heteroaryl group is preferably 1-3, more preferably 1-2.
  • Heteroatoms include, for example, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • Heteroaryl groups preferably have one or more nitrogen atoms.
  • Two R 2 groups in general formula (6) may be the same or different.
  • Two R 3 groups in formula (6) may be the same or different.
  • R 4 is preferably a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a group represented by -BR 4x R 4y , and is preferably a hydrogen atom, an alkyl group, an aryl group, or -BR 4x R 4y A group represented by —BR 4x R 4y is particularly preferable.
  • the substituent represented by R 4x R 4y is preferably a halogen atom, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group, more preferably an alkyl group, an aryl group, or a heteroaryl group, and particularly preferably an aryl group. These groups may further have a substituent.
  • Two R 4 groups in general formula (6) may be the same or different.
  • pyrrolopyrrole compounds are shown below.
  • Me represents a methyl group
  • Ph represents a phenyl group.
  • pyrrolopyrrole compound for example, paragraphs 0016 to 0058 of JP-A-2009-263614, paragraphs 0037-0052 of JP-A-2011-68731, paragraphs 0014-0027 of JP-A-2014-130343, international Examples include compounds described in paragraphs 0010-0033 of Publication No. 2015/166873. In addition, embodiment of this invention is not limited to these.
  • naphthalocyanine compound is preferably a compound represented by the following general formula (7).
  • R 1 to R 24 each independently represent a hydrogen atom, a halogen atom, a nitro group, a nitrile group, a carboxyl group, a sulfone group, an optionally substituted alkyl group, or a substituent.
  • optionally substituted aryl group optionally substituted cycloalkyl group, optionally substituted alkoxyl group, optionally substituted aryloxy group, optionally substituted an optionally substituted alkylthio group, an optionally substituted arylthio group, an optionally substituted alkylamino group, an optionally substituted arylamino group, or an optionally substituted sulfamoyl group
  • Z is a polymer site containing a monomer unit represented by general formula (8) or a phosphorus compound site represented by general formula (9), and * is a bond with Al.
  • X represents -CONH-R 25 -, -COO-R 26 -, -CONH-R 27 -O-, or -COO-R 28 -O-
  • R 25 to R 28 represents an alkylene group or an arylene group optionally linked by -O-, -CO-, -COO-, -OCO-, -CONH- or -NHCO- between carbon atoms.
  • R31 represents a hydrogen atom or a methyl group.
  • R 29 and R 30 each independently represent a hydroxyl group, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted It represents an alkoxyl group or an optionally substituted aryloxy group, and R 29 and R 30 may combine with each other to form a ring.
  • naphthalocyanine compounds are shown below. In addition, this invention is not limited to these.
  • the content of the near-infrared absorbent (E) is preferably 0.005 to 50% by mass, more preferably 0.01 to 40% by mass, based on the non-volatile content of the composition.
  • the content of the ultraviolet absorber can be designed according to the desired spectral cut rate.
  • compositions of embodiments of the present invention may contain a resin.
  • Resins include, for example, thermoplastic resins, photocurable resins, and thermosetting resins.
  • thermoplastic resins include polyolefin resins, polycarbonate resins, polyacrylic resins, polyester resins, polyamide resins, polyetherimide resins, cycloolefin resins, and the like.
  • Polyolefin resins include, for example, polyethylene, polypropylene, polybutene-1, poly-4-methylpentene, and copolymers thereof.
  • polyethylene include low-density polyethylene, high-density polyethylene, and the like.
  • Polypropylene includes, for example, crystalline or amorphous polypropylene. Copolymers using these include, for example, ethylene-propylene random, block or graft copolymers, ⁇ -olefin and ethylene or propylene copolymers, ethylene-vinyl acetate copolymers, ethylene-methyl acrylate copolymers.
  • polymers ethylene-ethyl acrylate copolymers, ethylene-acrylic acid copolymers, and the like.
  • crystalline or amorphous polypropylene and ethylene-propylene random, block or graft copolymers are preferred, and propylene-ethylene block copolymers are more preferred.
  • polypropylene-based resins are preferable from the viewpoint of being inexpensive and having a small specific gravity, so that the weight of molded articles can be reduced.
  • the number average molecular weight of polyolefin resin is about 30,000 to 500,000.
  • the melt flow rate (MFR) of the polyolefin resin is preferably 1 to 100 (g/10 minutes). Note that MFR is a numerical value determined according to JISK-7210.
  • polycarbonate resin is an amorphous resin, and is synthesized by reacting an aromatic dihydroxy compound with a carbonate precursor such as phosgene or carbonic acid diester.
  • a carbonate precursor such as phosgene or carbonic acid diester.
  • interfacial methods are preferred.
  • a transesterification method in which the reaction is performed in a molten state is preferred.
  • Aromatic dihydroxy compounds are, for example, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2 - bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxy-3-t-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5- bis(hydroxyaryl)alkanes such as dibromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane; 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1- bis(hydroxyaryl)
  • carbonate precursors examples include diaryl carbonates such as phosgene, diphenyl carbonate and ditolyl carbonate; dialkyl carbonates such as dimethyl carbonate and diethyl carbonate;
  • the aromatic dihydroxy compound and the carbonate precursor can each be used alone or in combination of two or more.
  • the viscosity average molecular weight of the polycarbonate resin is preferably 15,000 to 30,000, more preferably 16,000 to 27,000.
  • the viscosity-average molecular weight in this specification is a value converted from solution viscosity measured at a temperature of 25° C. using methylene chloride as a solvent.
  • polycarbonate resins include, for example, Iupilon H-4000 (manufactured by Mitsubishi Engineering-Plastics, viscosity average molecular weight 16,000), Iupilon S-3000 (Mitsubishi Engineering-Plastics, viscosity average molecular weight 23,000), and Iupilon E-2000. (manufactured by Mitsubishi Engineering Plastics Co., Ltd., viscosity average molecular weight 27,000).
  • polyacrylic resin is a compound obtained by polymerizing monomers such as methyl methacrylate and/or ethyl methacrylate and optionally other monomers by a known method.
  • examples of polyacrylic resins include ethylene-methyl acrylate copolymers, ethylene-ethyl acrylate copolymers, ethylene-acrylic acid copolymers, and the like.
  • monomers such as butadiene, ⁇ -methylstyrene, and maleic anhydride can be added for polymerization, and the heat resistance, fluidity, and impact resistance can be adjusted by adjusting the monomer weight and molecular weight.
  • Polyester resin is a resin having an ester bond in the main chain of the molecule, and polycondensate synthesized from dicarboxylic acid (including derivatives thereof) and diol (dihydric alcohol or dihydric phenol); including) and a polycondensate synthesized from a cyclic ether compound; and a ring-opening polymer of a cyclic ether compound.
  • the polyester resin includes a homopolymer obtained by polymerizing a dicarboxylic acid and a diol, a copolymer using a plurality of raw materials, a polymer blend obtained by mixing these materials, and the like.
  • the dicarboxylic acid derivatives include acid anhydrides, esters and the like. There are two kinds of dicarboxylic acids, aliphatic and aromatic dicarboxylic acids, and aromatic dicarboxylic acids are more preferable from the viewpoint of improving heat resistance.
  • Aromatic dicarboxylic acids are, for example, terephthalic acid, isophthalic acid, phthalic acid, chlorophthalic acid, nitrophthalic acid, p-carboxylphenylacetic acid, m-phenylenediglycolic acid, p-phenylenediglycolic acid, diphenyldiacetic acid, diphenyl-p , p'-dicarboxylic acid, diphenyl-4,4'-diacetic acid, diphenylmethane-p,p'-dicarboxylic acid, diphenylethane-m,m'-dicarboxylic acid, stilbenzylcarboxylic acid, diphenylbutane-p,p' -dicarboxylic acid, benzophenone-4,4'-dicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-1,5-dicarboxylic acid, naphthalene-2,6-
  • aliphatic dicarboxylic acids examples include oxalic acid, succinic acid, adipic acid, corcic acid, mazelaic acid, sebacic acid, dodecanedicarboxylic acid, undecanedicarboxylic acid, maleic acid, and fumaric acid.
  • Dihydric alcohols are, for example, ethylene glycol, trimethylene glycol, butane-1,3-diol, butane-1,4-diol, 2,2-dimethylpropane-1,4-diol, cis-2-butene-1 ,4-diol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, octamethylene glycol, decamethylene glycol, cyclohexanedimethanol and the like.
  • ethylene glycol, butane-1,4-diol and cyclohexanedimethanol are preferred.
  • Dihydric phenols include, for example, hydroquinone, resorcinol, bisphenol A and the like.
  • Examples of cyclic ether compounds include ethylene oxide and propylene oxide.
  • Dicarboxylic acids and dihydric alcohols can be used either alone or in combination of two or more.
  • polyamide resin is a crystalline resin, and can be synthesized, for example, by subjecting a carboxylic acid component and a compound (Am) having two or more amino groups to a dehydration condensation reaction.
  • Carboxylic acid components include, for example, adipic acid, sebacic acid, isophthalic acid, and terephthalic acid.
  • a compound having 3 or more carboxyl groups can be used as the carboxylic acid component.
  • Known compounds (Am) having two or more amino groups can be used, for example, ethylenediamine, propylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, triethylene Aliphatic polyamines such as tetramine; Aliphatic polyamines including alicyclic polyamines such as isophoronediamine and dicyclohexylmethane-4,4'-diamine; Aromatic polyamines such as phenylenediamine and xylylenediamine; 1,3-diamino-2 -propanol, 1,4-diamino-2-butanol, 1-amino-3-(aminomethyl)-3,5,5
  • polyetherimide resin is an amorphous resin having a glass transition temperature of more than 180° C., and has good transparency, high strength, high heat resistance, high elastic modulus, and broad chemical resistance. As such, they are widely used in diverse applications such as automotive, telecommunications, aerospace, electrical/electronics, transportation and healthcare.
  • One process for making polyetherimide resins is by polymerization of alkali metal salts of dihydroxyaromatic compounds, such as bisphenol A disodium salt (BPA.Na 2 ), and bis(halophthalimide). The molecular weight of the resulting polyetherimide can be controlled in two ways.
  • the first method is to use a molar excess of bis(halophthalimide) to the alkali metal salt of the dihydroxyaromatic compound.
  • a second method is to prepare the bis(halophthalic anhydride) in the presence of a monofunctional compound such as phthalic anhydride which forms an endcapping agent.
  • Phthalic anhydride reacts with some of the organic diamines to form monohalo-bis(phthalimides).
  • Monohalo-bis(phthalimides) serve as end-capping agents in the polymerization step by reacting with phenoxide end groups in growing polymer chains.
  • Commercially available polyetherimide resins include, for example, ULTEM (manufactured by Saudi Basic Industries Corporation).
  • cycloolefin resin is an amorphous resin having an alicyclic structure in its main chain and/or side chains.
  • Types of alicyclic structures include, for example, norbornene polymers, monocyclic cyclic olefin polymers, cyclic conjugated diene polymers, vinyl alicyclic hydrocarbon polymers, and hydrides thereof.
  • the norbornene polymer is preferred because of its excellent moldability and transparency.
  • Norbornene monomers include, for example, bicyclo[2.2.1]hept-2-ene (common name: norbornene), tricyclo[4.3.0.12,5]deca-3,7-diene (common name : dicyclopentadiene), 7,8-benzotricyclo[4.3.0.12,5]dec-3-ene (common name: methanotetrahydrofluorene), tetracyclo[4.4.0.12,5. 17,10]dodeca-3-ene (common name: tetracyclododecene) and the like.
  • Examples of commercially available cycloolefin resins include Topas (manufactured by Polyplastics) and APEL (manufactured by Mitsui Chemicals, Inc.).
  • Polyvinyl acetal resin is preferably polyvinyl acetal obtained by acetalizing polyvinyl alcohol with aldehyde. Polyvinyl acetal resins are preferred over polyvinyl butyral resins. Polyvinyl butyral resin can be synthesized, for example, by reacting polyvinyl alcohol and butyraldehyde under acidic conditions.
  • thermoplastic resin can be used alone or in combination of two or more.
  • the content of the ultraviolet absorber is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 1 part by mass, with respect to 100 parts by mass of the thermoplastic resin.
  • a composition containing an ultraviolet absorber and a thermoplastic resin is preferably produced, for example, as a masterbatch in which the ultraviolet absorber is blended at a high concentration.
  • a masterbatch is prepared and then melted and kneaded with a diluent resin (thermoplastic resin) to prepare a molded article
  • the UV absorber is more uniform in the molded article than a molded article prepared without the masterbatch. It is easy to disperse in water, and aggregation of the ultraviolet absorber can be suppressed. This improves the transparency of the molded article.
  • the masterbatch can be produced, for example, by melt-kneading an ultraviolet absorber and a thermoplastic resin and using a pelletizer to produce pellets.
  • the ultraviolet absorber In order to prevent aggregation of the ultraviolet absorber, it is preferable to melt-knead the ultraviolet absorber and wax in advance to prepare a dispersion, and then melt-knead the dispersion together with the thermoplastic resin to prepare a masterbatch.
  • a blend mixer or a three-roll mill for preparation of the dispersion.
  • the blending amount of the ultraviolet absorber is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 3 parts by mass, with respect to 100 parts by mass of the thermoplastic resin.
  • composition of the embodiment of the present invention can be prepared into a molded body by preparing a liquid masterbatch and then melt-kneading it with a diluent resin (thermoplastic resin).
  • a liquid masterbatch is obtained by dissolving or dispersing an ultraviolet absorber in a liquid resin.
  • a liquid resin is a resin with a viscosity of 8,000 mPa ⁇ s or less at 25°C.
  • the viscosity is preferably 10 to 5,000 mPa ⁇ s, more preferably 100 to 3,000 mPa ⁇ s.
  • the ultraviolet absorber can be easily dispersed in the liquid masterbatch. Viscosity in this specification is a value measured at 25° C. using a Brookfield viscometer according to JIS K7117-1:1999.
  • the content of the liquid resin is preferably 50% by mass or more, more preferably 60 to 95% by mass, and even more preferably 70 to 90% by mass, based on 100 parts by mass of the liquid masterbatch.
  • the melt viscosity can be suppressed during melt kneading, making it easier to disperse the ultraviolet absorber.
  • Using this liquid masterbatch gives a molded article with high transparency.
  • the number average molecular weight (Mn) of the liquid resin is preferably 100-3000, more preferably 200-2000, even more preferably 500-1500, and particularly preferably 1000-1500.
  • Mn is 100 or more, it is easy to achieve both moldability and transparency of the molded product. Further, when Mn is 3000 or less, dispersibility and antistatic properties are improved.
  • Liquid resins include, for example, epoxy resins such as epoxidized soybean oil and epoxidized linseed oil, aliphatic polyester resins, polyalkylene glycol resins, polyether ester resins, and tributyl acetylcitrate. Even when high molding temperatures such as polyethylene terephthalate (PET) and polycarbonate are required, aliphatic polyesters, polyalkylene glycol resins, polyether ester resins, or acetyl citric acid resins are used because they have high heat resistance and excellent antistatic properties. Tributyl is preferred.
  • An aliphatic polyester resin is a resin obtained by reacting an aliphatic polyhydric carboxylic acid and a polyhydric alcohol.
  • An aliphatic polycarboxylic acid is an aliphatic carboxylic acid having two or more carboxyl groups.
  • Aliphatic polycarboxylic acids include, for example, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, tricarballylic acid, 1,3,6-hexanetricarboxylic acid, 1 , 3,5-hexanetricarboxylic acid and the like.
  • a polyhydric alcohol is an alcohol having two or more hydroxyl groups.
  • Polyhydric alcohols are, for example, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,3-butanediol, 2-methyl-1,3-propanediol, 1 ,4-butanediol, 1,5-pentanediol, 2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2-n-butyl-2-ethyl-1 ,3-propanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, 2-ethyl-1,3-hexanediol, Aliphatic glycols such as 2-methyl-1,8-octaned
  • Aliphatic carboxylic acids and polyhydric alcohols can be used alone or in combination of two or more.
  • the freezing point of the aliphatic polyester resin is preferably -5°C or lower, more preferably -50°C to -10°C.
  • Adekasizer PN-170 manufactured by ADEKA Co., Ltd., viscosity at 25 ° C.: 800 mPa s, freezing point -15 ° C., adipate polyester
  • Adekasizer P-200 (ADEKA Co., Ltd. manufactured by ADEKA CORPORATION, viscosity at 25 ° C. 2,600 mPa s, freezing point -20 ° C., adipate polyester
  • ADEKA CIZER PN-250 manufactured by ADEKA Co., Ltd., viscosity at 25 ° C. 4,500 mPa s, freezing point -20 ° C., adipic acid polyester
  • a polyether resin is a resin having repeating units of alkyleneoxy groups.
  • the number of carbon atoms in the alkyleneoxy group is preferably 1-6.
  • the polyether resin preferably has a viscosity of 10,000 mPa ⁇ s or less at 25°C. This viscosity is suitable for use in liquid masterbatch applications.
  • the number of carbon atoms in the alkyleneoxy group is preferably 2-4. While compatibility improves by this, water absorption can be suppressed.
  • Polyether resins include, for example, polyethylene glycol each having 2 carbon atoms in the repeating unit, polytrimethylene glycol and polypropylene glycol both having 3 carbon atoms in the repeating unit, and carbon Examples include polytetramethylene glycol and polybutylene glycol having a number of four.
  • polyether ester resin is an ester compound of an aliphatic polycarboxylic acid resin and an alkylene glycol resin.
  • polyetherester resins include, for example, Adekasizer RS-107 (manufactured by ADEKA Co., Ltd., viscosity at 25°C: 20 mPa s, freezing point: -47°C, adipate ether ester resin), Adekasizer RS-700 ( manufactured by ADEKA Co., Ltd., viscosity at 25° C. of 30 mPa ⁇ s, freezing point of ⁇ 53° C., polyether ester resin) and the like.
  • Adekasizer RS-107 manufactured by ADEKA Co., Ltd., viscosity at 25°C: 20 mPa s, freezing point: -47°C, adipate ether ester resin
  • Adekasizer RS-700 manufactured by ADEKA Co., Ltd., viscosity at 25° C. of 30 mPa ⁇ s, freezing point of ⁇ 53° C., polyether ester resin
  • the freezing point of the polyetherester resin is preferably -5°C or lower, more preferably -50°C to -10°C.
  • a molded body can be produced by preparing a plasticizer dispersion and then melt-kneading it with a diluent resin (thermoplastic resin).
  • the content of the ultraviolet absorber is preferably 0.1 to 30% by mass in the plasticizer dispersion.
  • a plasticizer dispersion is prepared by dissolving or dispersing an ultraviolet absorber in a plasticizer.
  • plasticizers include phthalates, adipates, trimellitates, polyesters, phosphates, citrates, epoxidized vegetable oils, and sebacates.
  • plasticizers include phthalates, adipates, trimellitates, polyesters, phosphates, citrates, epoxidized vegetable oils, and sebacates.
  • triethylene glycol-di-2-ethylhexanoate and triethylene glycol-di-n-heptanoate are preferred, and triethylene glycol-di-2-ethylhexanoate is more preferred.
  • the plasticizer can be used alone or in combination of two or more.
  • the content of the plasticizer is preferably 60 to 99.9% by mass in the plasticizer dispersion.
  • the liquid masterbatch and plasticizer dispersion in the present invention may contain a resin type dispersant.
  • the UV absorber is more uniformly dispersed in the liquid masterbatch and the plasticizer dispersion, so that the molded article has even higher transparency.
  • the storage stability of the liquid masterbatch and the plasticizer dispersion is improved by containing the resin type dispersant.
  • the resin-type dispersant is a resin that has an adsorption site that has the property of adsorbing to the ultraviolet absorber and the colorant, and a relaxation site that is compatible with components other than the ultraviolet absorber and the colorant.
  • the resin-type dispersant include basic dispersants, acidic dispersants, neutral dispersants, amphoteric dispersants, and the like.
  • the main skeleton of the resin-type dispersant is, for example, a polyurethane skeleton, a polyolefin skeleton, a poly(meth)acrylic skeleton, a polyester skeleton, a polyamide skeleton, a polycarbonate skeleton, a polyether skeleton, a polysiloxane skeleton, a polyvinyl skeleton, a polyimide skeleton, a polyurea skeleton, or the like. and composite resins of these skeletons may also be used.
  • the molecular structure of the resin-type dispersant is not limited, and examples thereof include a random structure, a block structure, a chain structure, a comb-like structure, a star-like structure, and the like.
  • the resin-type dispersant has an acidic group or a basic group, some or all of them may be neutralized.
  • acidic groups include sulfo groups, phenol moieties, phosphoric acid groups and carboxyl groups. Among these, a carboxyl group is preferred.
  • Basic groups include primary amino groups, secondary amino groups, tertiary amino groups, and quaternary ammonium salt moieties. Among them, a tertiary amino group and a quaternary ammonium salt moiety are preferred.
  • a resin type dispersant having a basic functional group and a polymeric dispersant having a basic functional group are preferred because the viscosity of the dispersion is lowered with a small addition amount.
  • Polymers, nitrogen atom-containing acrylic block copolymers, urethane resin type dispersants and urethane polymer dispersions having functional groups containing tertiary amino groups, quaternary ammonium bases, nitrogen-containing heterocycles, etc. in side chains agents and the like are preferred.
  • the resin-type dispersant can be used alone or in combination of two or more.
  • the content of the resin-type dispersant is preferably about 5-200% by mass, more preferably about 10-100% by mass, relative to 100 parts by mass of the ultraviolet absorber.
  • resin-type dispersants include, for example, Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166 manufactured by BYK-Chemie Japan.
  • the resin-type dispersant When the resin-type dispersant is dissolved in an organic solvent, it is preferable to add the liquid resin, heat under reduced pressure, and distill off the solvent before use. In that case, since the liquid masterbatch containing this also does not contain an organic solvent, it is easy to use in the process.
  • a liquid masterbatch can be produced by mixing an ultraviolet absorber and a liquid resin.
  • a resin-type dispersant for the production.
  • a device such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor can be used for mixing.
  • a plasticizer dispersion can be prepared by mixing an ultraviolet absorber and a plasticizer.
  • a resin-type dispersant for the production.
  • the apparatus described in the above "method for producing liquid masterbatch" can be used.
  • composition of the present specification can contain antioxidants, light stabilizers, dispersants, waxes, etc. as optional components in addition to thermoplastic resins and ultraviolet absorbers.
  • a composition containing an ultraviolet absorber and a thermoplastic resin can be used, for example, as a paint.
  • thermoplastic resin preferably has a glass transition temperature of 30°C or higher.
  • thermoplastic resins include nitrocellulose and polyester.
  • the paint may contain a resin-type dispersant having a carboxyl group as a resin-type dispersant.
  • the molecular structure of the resin-type dispersant having a carboxyl group may be comb-shaped or linear.
  • Comb-shaped resin-type dispersant examples include the following (S1) or (S2).
  • the resin-type dispersant (S1) can be produced by known methods such as those disclosed in International Publication No. 2008/007776, JP-A-2008-029901, and JP-A-2009-155406.
  • a resin-type dispersant that is a reaction product of a hydroxyl group of a polymer having a hydroxyl group and an acid anhydride group of a tetracarboxylic dianhydride; and a hydroxyl group of a compound having a hydroxyl group and a tetracarboxylic dianhydride.
  • resin-type dispersants which are polymers obtained by polymerizing ethylenically unsaturated monomers in the presence of reaction products with acid anhydride groups.
  • the resin type dispersant (S2) is manufactured by known methods such as WO 2008/007776, JP 2009-155406, JP 2010-185934, and JP 2011-157416. can be done. For example, in the presence of a reaction product of a hydroxyl group of a compound having a hydroxyl group and an acid anhydride group of a tetracarboxylic dianhydride, a hydroxyl group, a t-butyl group, an oxetane skeleton, or a thermal cross-linking group such as a blocked isocyanate is present.
  • a resin-type dispersant having a side chain obtained by polymerizing an ethylenically unsaturated monomer and other substances; a resin-type dispersant obtained by further reacting an ethylenically unsaturated monomer having an isocyanate group with the hydroxyl group of the side chain. etc.
  • Linear resin-type dispersant A linear resin-type dispersant can be produced using a known method. can be synthesized using a known method as shown in .
  • a dispersant having a carboxyl group can be produced by adding a tricarboxylic acid anhydride to the hydroxyl group of a vinyl polymer having one hydroxyl group at one end. can be done.
  • resin-type dispersants have an affinity site that has the property of adsorbing to the ultraviolet absorber and the colorant, and a site that is compatible with the ultraviolet absorber and the colorant carrier. Any material can be used as long as it has an action of adsorbing to the material and stabilizing the dispersion in the colorant carrier.
  • polymeric dispersants having basic functional groups include nitrogen atom-containing graft copolymers, nitrogen atom-containing acrylic resins having functional groups containing tertiary amino groups, quaternary ammonium bases, nitrogen-containing heterocycles, etc. in side chains. system block copolymers and urethane polymer dispersants.
  • the composition can be used, for example, for coating layers such as hard coat layers, top coat layers, and intermediate layers of various laminates.
  • the composition preferably contains an ultraviolet absorber, a photopolymerizable compound and a photopolymerization initiator.
  • the ultraviolet absorber in the composition contains a photocurable site.
  • the composition can also contain a resin.
  • the composition can contain known additives for photocurable compositions and, if necessary, an organic solvent.
  • Photopolymerizable compounds include monomers and oligomers. Photopolymerizable compounds include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, ⁇ -carboxyethyl (meth) ) acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, phenoxy Tetraethylene glycol (meth)acrylate, phenoxyhexaethyleneglycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acryl
  • Photopolymerization initiators include, for example, acetophenone acetophenone ring-containing compounds, benzoin ring-containing compounds, benzophenone ring-containing compounds, thioxanthone ring-containing compounds, triazine ring-containing compounds, oxime ester compounds, phosphine compounds, quinone compounds, and borate compounds. , carbazole ring-containing compounds, imidazole ring-containing compounds, titanocene compounds, and the like. Among these, oxime ester compounds are preferred in terms of high sensitivity.
  • the composition can be used, for example, for paints and adhesives.
  • the composition preferably contains an ultraviolet absorber and a thermosetting resin, and further preferably contains a curing agent.
  • the composition preferably contains an ultraviolet absorber, a thermosetting resin (adhesive resin), and a curing agent.
  • the adhesive resin is a resin with a glass transition temperature of -50 to -20°C.
  • Types of adhesive resins include, for example, acrylic resins, polyesters, and urethane resins.
  • the adhesive resin preferably has a functional group capable of reacting with the curing agent. Functional groups include, for example, carboxyl groups and hydroxyl groups.
  • Curing agents include, for example, isocyanate curing agents, epoxy curing agents, aziridine curing agents, and metal chelate curing agents.
  • a molded article according to an embodiment of the present invention can be produced by melting and kneading a composition containing an ultraviolet absorber, a resin, and the like, and molding the composition.
  • the composition is a masterbatch
  • the molded article is obtained by putting resin into a mold. Molded articles include articles and molded articles obtained without using a mold, such as plastic films.
  • the diluent resin it is preferable to use the already explained thermoplastic resin.
  • melt-kneading it is preferable to use, for example, a single-screw kneading extruder, a twin-screw kneading extruder, a tandem-type twin-screw kneading extruder, or the like.
  • the melt-kneading temperature varies depending on the type of thermoplastic resin, but is usually about 150 to 320°C.
  • molding methods include extrusion molding, injection molding, and blow molding.
  • extrusion molding include compression molding, pipe extrusion molding, laminate molding, T-die molding, inflation molding, and melt spinning.
  • the molding temperature is usually 160-320°C, depending on the softening point of the diluted resin.
  • the molded bodies of the embodiments of the present invention can be used for pharmaceutical packaging materials, food packaging materials, displays, glass interlayer films, optical lenses, solar cells, window films, and spectacle lenses, for example.
  • thermoplastic resins such as polyester resins and cycloolefin resins. These molded articles have improved flexibility and visibility, and can suppress deterioration of contents.
  • Molded articles that can be used for displays, glass interlayer films, optical lenses, and solar cell applications may be any molded articles that are made of thermoplastic resin, but are made of a resin that has a property of being transparent to a desired wavelength. A film is preferred.
  • resins constituting such a molded body include polyetherimide resins, polyethersulfone resins, polyethylene terephthalate resins, polyimide resins, polysulfone resins, polyarylate resins, polyamides, polycarbonate resins, alicyclic Structured olefin polymer-based resins (alicyclic olefin polymer-based resins), cellulose ester-based resins, and the like are included.
  • the coating film of the embodiment of the present invention can be produced by coating a substrate or the like with a composition containing an ultraviolet absorber and a resin, and a paint containing an organic solvent and the like, followed by drying.
  • a composition containing an ultraviolet absorber and a resin and a paint containing an organic solvent and the like, followed by drying.
  • examples thereof include a hard coat layer, a top coat layer, a coating layer such as an intermediate layer of various laminates, and an adhesive layer.
  • Coating layers such as hard coat layers, top coat layers, intermediate layers of various laminates, for example, display materials, sensor materials, optical control materials, various industrial coating materials, automobile parts, home appliances, housing, etc. In applications such as building materials and toiletry products, it can be applied to base materials to form a film that blocks ultraviolet rays and suppress deterioration of organic materials.
  • the adhesive layer can be coated on a release sheet and dried to form an adhesive layer, and a base material can be attached to the adhesive layer to produce an adhesive sheet.
  • the pressure-sensitive adhesive sheet of the present specification is used, for example, in displays (e.g., televisions, personal computers, smartphones, etc.), automotive parts, sensor members, home appliances, building materials for housing, glass interlayer applications, etc. It is preferable to use it by laminating to.
  • the adhesive sheet absorbs ultraviolet light contained in backlight and sunlight, and light in the short wavelength region of visible light, and suppresses adverse effects on the eyes and the human body. and deterioration of the display element of the display can be suppressed.
  • Sheet, film and tape are synonyms.
  • the laminated body using the molded article or the coating film of the embodiment of the present invention can suppress adverse effects on the eyes by absorbing light in the short wavelength region of ultraviolet rays and visible light contained in the backlight of the display.
  • deterioration of the display element of the display can be suppressed by absorbing light in the short wavelength region of ultraviolet light and visible light contained in sunlight.
  • a laminated glass using a molded article containing the above composition absorbs light in the short wavelength region of ultraviolet light and visible light contained in sunlight, thereby suppressing adverse effects on the eyes and the human body.
  • lens applications for example, it can be used in lenses that can be used in eyeglasses and optical sensors.
  • a lens using a molded body containing the above composition for example, for spectacle applications, absorbs light in the short wavelength region of ultraviolet light and visible light contained in sunlight, thereby suppressing adverse effects on the eyes and the human body.
  • optical sensor applications it is possible to increase the sensitivity of the sensor by cutting unnecessary wavelengths of light that can become noise.
  • ultraviolet rays and light in the visible light short wavelength region of about 400 to 420 nm deteriorate resins, so the use of the ultraviolet absorber of the embodiment of the present invention can reduce the deterioration of resins in general applications using resins. Therefore, it is possible to extend the life of the molded article and coating film, and as a result, reduce the amount of waste.
  • a numerical range indicated using “to” indicates a range that includes the numerical values before and after “to” as the minimum and maximum values, respectively.
  • the upper limit or lower limit of the numerical range in one step can be arbitrarily combined with the upper limit or lower limit of the numerical range in another step.
  • the present invention relates to the subject matter of Japanese Patent Application No. 2021-116306 filed on July 14, 2021, the entire disclosure of which is incorporated herein by reference.
  • ⁇ Method for producing ultraviolet absorbing dye (A-1)> Ultraviolet absorbing dye A-1) 160 parts of nitrobenzene, 8 parts of cyanuric chloride and 17.4 parts of aluminum chloride were placed in a 300 mL Erlenmeyer flask and stirred to suspend. Next, while cooling with ice water, 21.9 parts of 2-naphthol was added little by little. Thereafter, the mixture was stirred overnight while gradually returning to room temperature to obtain a reaction liquid (A'-1). On the other hand, a 500 mL beaker was charged with 38.1 parts of water, 10.0 parts of 35% hydrochloric acid and 45.0 parts of methanol, and the reaction solution (A'-1) was added dropwise little by little. After stirring for 30 minutes, the mixture was filtered to obtain a wet cake (a-1) containing the ultraviolet absorbing dye (A-1).
  • ICP emission spectrometry was used to measure the metal component (B) of the ultraviolet absorber of the embodiment of the present invention.
  • ⁇ Measurement conditions About 0.2 g of the ultraviolet absorber 1 was precisely weighed and subjected to decomposition treatment (2 mL of nitric acid for precision analysis was added as a decomposition reagent) using a microwave sample pretreatment device (MLS-1200MEGA manufactured by Milestone General). Next, ultrapure water is added to the resulting decomposed solution, and 25 mL of the filtered filtrate is placed in a constant volume in a volumetric flask. This solution was measured by ICP emission spectrometry (720-ES ICP optical emission spectrometer manufactured by Varian Co., Ltd.) to quantify metal ions.
  • ICP emission spectrometry 720-ES ICP optical emission spectrometer manufactured by Varian Co., Ltd.
  • the content of the metal component (B) shown in this example means the total content of ions of Na, Mg, Al, K, Ca, and Fe.
  • the ultraviolet absorbing dye 1 Na: 1432 ppm, Mg: 836 ppm, Al: 42750 ppm, K: 147 ppm, Ca: 2428 ppm and Fe: 548 ppm were obtained.
  • the total value of metal component (B) was 48141 ppm.
  • the metal atoms were measured by ICP emission spectrometry, using UV absorber 1 as an example. Other UV absorbers were also measured in the same manner as above. Table 1 shows the measurement results.
  • X-ray diffractometer RINT2100 manufactured by Rigaku Corporation Sampling width: 0.02° Scan speed: 2.0°/min Divergence slit: 1° Divergence longitudinal limiting slit: 10mm Scattering slit: 2° Light receiving slit: 0.3mm Tube: Cu Tube voltage: 40kV Tube current: 40mA
  • Fig. 1 shows an example of a diffraction pattern obtained by powder X-ray diffraction of an ultraviolet absorber.
  • the X-axis is the Bragg angle (2 ⁇ )
  • the Y-axis is the diffraction peak intensity (count).
  • UV absorber 3 After obtaining the wet cake (a-3), 45 g of water was sprinkled to wash the cake, followed by filtration to obtain the wet cake (a-4). The resulting wet cake (a-4) was dried overnight at 80° C. to obtain UV absorber 3 containing UV absorbing dye (A-1).
  • UV absorber 14 300 parts of UV absorber 13, 1500 parts of sodium chloride, and 400 parts of diethylene glycol were charged into a 3 L double-arm kneader to form a dough, which was then kneaded at a material temperature of 60° C. for 6 hours. The resulting dough (kneaded mass) was taken out, reslurried in water of about 10 times the weight of the dough, stirred at 25°C for 1.5 hours, and filtered. Further, it was reslurried again, filtered and washed with water to obtain a paste pigment, and dried in a heating oven at 80° C. for 48 hours to obtain an ultraviolet absorber 14 containing an ultraviolet absorbing dye (A-1).
  • A-1 ultraviolet absorber 14 containing an ultraviolet absorbing dye
  • UV absorber 17 ⁇ Method for Producing UV Absorber 17>
  • methanesulfonic acid 40.0 parts of UV absorber 1 was gradually added with stirring, and dissolved by stirring for 4 hours. Next, the solution is gradually added dropwise to 50,000 parts of water at 0° C. over 30 minutes with stirring, filtered, washed with water, dried at 80° C., and an ultraviolet absorber containing the ultraviolet absorbing dye (A-1). 17 was obtained.
  • UV absorber 18 ⁇ Method for Producing UV Absorber 18>
  • UV absorber 18 35.0 parts of UV absorber 3 and 350 parts of diethylene glycol were mixed, and the mixture was heated and stirred at 120° C. for 3 hours. Filtration, washing with warm water, and drying at 80° C. were carried out to obtain an ultraviolet absorber 18 containing the ultraviolet absorbing dye (A-1) represented by general formula (1).
  • UV absorber 19 containing the UV absorbing dye (A-3) was obtained in the same manner as the UV absorber 17, except that the UV absorber 9 was used instead of the UV absorber 1.
  • UV absorber 20 A UV absorber 20 containing a UV absorbing dye (A-3) was obtained in the same manner as the UV absorber 18, except that the UV absorber 11 was used instead of the UV absorber 3.
  • UV Absorber 21 (Ultraviolet absorption dye A-4)
  • the ultraviolet absorbing dye (A-1) was produced in the same manner, except that 24.3 parts of 1,3-dihydroxynaphthalene was added instead of 21.9 parts of 2-naphthol.
  • a wet cake (a-19) containing 4) was obtained.
  • the wet cake (a-19) was washed by sprinkling 45 g of methanol and separated by filtration to obtain a wet cake (a-20).
  • the wet cake (a-20) was reslurried in 100 g of methanol at room temperature for 30 minutes, and filtered.
  • a UV absorbing dye (A-3) was produced in the same manner except that 9.1 parts of methyl 6-hydroxy-2-naphthoate was added instead of 6.5 parts of 2-naphthol.
  • a wet cake (a-22) containing (A-6) was obtained.
  • the wet cake (a-22) was washed by sprinkling 45 g of methanol and separated by filtration to obtain a wet cake (a-23). Then, the wet cake (a-23) was returned to 100 g of methanol, reslurried at room temperature for 30 minutes, and separated by filtration.
  • Ultraviolet absorber 23 was produced in the same manner except that 8.4 parts of 6-hydroxy-2-naphthoic acid was added instead of 9.1 parts of methyl 6-hydroxy-2-naphthoate. An ultraviolet absorber 24 containing agent (A-7) was obtained.
  • UV absorber 25 ⁇ Method for Producing UV Absorber 25> (Ultraviolet absorption dye A-8) Manufactured in the same manner as UV absorber 23, except that 11.0 parts of sodium 2-naphthol-6-sulfonate hydrate was added instead of 9.1 parts of methyl 6-hydroxy-2-naphthoate. to obtain UV absorber 25 containing UV absorber (A-8).
  • UV Absorber 26 (Ultraviolet absorbing dye A-9)
  • the ultraviolet absorbing dye (A-2) instead of 8 parts of 2,4-dichloro-6-phenyl-1,3,5-triazine, 12.8 parts of 2-naphthol and 11.8 parts of aluminum chloride, Manufactured in the same manner except that 8 parts of 2-(4-biphenylyl)-4,6-dichloro-1,3,5-triazine, 9.5 parts of 2-naphthol and 8.8 parts of aluminum chloride were added, A wet cake (a-25) containing the ultraviolet absorbing dye (A-9) was obtained.
  • the wet cake (a-25) was washed by sprinkling 45 g of methanol and separated by filtration to obtain a wet cake (a-26). Then, the wet cake (a-26) was returned to 100 g of methanol, reslurried at room temperature for 30 minutes, and separated by filtration. Furthermore, 45 g of water was sprinkled to wash the cake, and the cake was separated by filtration to obtain a wet cake (a-27). The obtained wet cake (a-27) was dried at 80° C. overnight to obtain an ultraviolet absorber 26 containing an ultraviolet absorbing dye (A-9).
  • UV Absorber 27 ⁇ Method for Producing UV Absorber 27> (Ultraviolet absorption dye A-10) 8 parts of UV absorber 1 and 80 parts of N-methyl-2-pyrrolidone were placed in a 300 mL Erlenmeyer flask and dissolved by stirring. Next, 5.4 parts of tripotassium phosphate was charged and stirred to suspend. Then, 5.8 parts of 1-iodobutane was charged, heated to 110° C. with stirring, and stirred for 3 hours to obtain a reaction liquid. On the other hand, 400 parts of water was charged into a 1 L beaker, and the reaction liquid was added dropwise little by little. After stirring overnight, the mixture was filtered to obtain a wet cake (a-28).
  • UV absorber 1 8 parts of UV absorber 1 and 80 parts of N-methyl-2-pyrrolidone were placed in a 300 mL Erlenmeyer flask and dissolved by stirring. Next, 5.4 parts of tripotassium
  • the wet cake (a-28) was reslurried in 400 g of water, stirred for 3 hours, and filtered to obtain a wet cake (a-29).
  • the resulting wet cake (a-29) was dried overnight at 80° C., and the resulting dried product was pulverized with 80 mesh to obtain UV absorber 27 containing UV absorbing dye A-10.
  • the obtained wet cake (a-30) was filtered off, reconstituted with 100 parts of methyl ethyl ketone, and stirred at 40° C. for 30 minutes. Then, 100 parts of methanol was added, and the mixture was stirred for 30 minutes while cooling with ice, and filtered. The resulting wet cake (a-31) was returned to 100 parts of methanol, stirred for 30 minutes, and filtered. The resulting wet cake (a-32) was dried overnight at 80° C. to obtain UV absorber 28 containing UV absorbing dye A-11.
  • the obtained wet cake (a-36) was filtered, and the obtained wet cake (a-36) was returned to 100 parts of methanol, stirred for 30 minutes, and filtered. Then, the obtained wet cake (a-37) was returned to 100 parts of water, stirred for 30 minutes, and filtered.
  • the obtained wet cake (a-38) was dried under reduced pressure at 60° C. to obtain UV absorber 30 containing UV absorbing dye A-13.
  • Comparative material 1 ⁇ Manufacturing method of comparative material 1>
  • the wet cake (a-1) was dried overnight at 80° C. to obtain Comparative Material 1 containing the UV-absorbing dye (A-1) represented by general formula (1).
  • Comparative material 3 ⁇ Manufacturing method of comparative material 3>
  • the wet cake (a-6) was dried overnight at 80° C. to obtain Comparative Material 3 containing the UV-absorbing dye (A-2) represented by general formula (1).
  • Comparative material 4 Water was added to the reaction solution (A'-2) to carry out extraction/liquid separation operations, and 5% aqueous sodium bicarbonate solution and saturated brine were added to the obtained organic layer to separate the layers. The obtained organic layer was concentrated under reduced pressure to obtain Comparative Material 4.
  • Comparative material 5 ⁇ Manufacturing method of comparative material 5>
  • the wet cake (a-11) was dried overnight at 80° C. to obtain Comparative Material 5 containing UV absorbing dye (A-3).
  • Comparative material 6 Water was added to the reaction solution (A'-3) to carry out an extraction/liquid separation operation, and 5% aqueous sodium bicarbonate solution and saturated brine were added to the resulting organic layer to separate the layers. The obtained organic layer was concentrated under reduced pressure to obtain Comparative Material 6.
  • Comparative material 7 35.0 parts of Comparative Material 1 and 350 parts of diethylene glycol were mixed, and the mixture was heated and stirred at 120° C. for 3 hours. Filtration, washing with warm water, and drying at 80° C. gave Comparative Material 7 containing the UV-absorbing dye (A-1) represented by the general formula (1).
  • Comparative material 8 To 1000 parts of methanesulfonic acid, 40.0 parts of Comparative Material 2 was gradually added with stirring, and dissolved by stirring for 4 hours. Then, the solution was gradually added dropwise to 50,000 parts of water at 0° C. over 30 minutes with stirring, filtered, washed with water, dried at 80° C., and comparative material 8 containing ultraviolet absorbing dye (A-1). got
  • Comparative material 9 A comparative material 9 containing an ultraviolet absorbing dye (A-3) was obtained in the same manner as the comparative material 7 except that the comparative material 5 was used instead of the comparative material 1.
  • Comparative material 10 A comparative material 10 containing an ultraviolet absorbing dye (A-3) was obtained in the same manner as in the production of comparative material 8, except that comparative material 6 was used instead of comparative material 2.
  • Table 1 shows the metal amounts and X-ray diffraction peak ratios of the obtained UV absorbers 1 to 30 and comparative materials 1 to 10.
  • UV-visible absorption spectrum was measured for UV absorbers 1-30 and comparative materials 1-10. Table 2 shows the results. Moreover, the solution preparation method for absorbance measurement and the measurement conditions are as follows.
  • Example 1-1 1 part of UV absorber 1 and 1000 parts of tetrahydrofuran were mixed and dissolved completely. Subsequently, 2 parts of the previous solution and 98 parts of tetrahydrofuran were uniformly mixed to prepare a solution having a concentration of 20 ppm.
  • the concentrations of ultraviolet absorbers 2 to 30 and comparative materials 1 to 10 were also adjusted as shown in Table 2.
  • Evaluation criteria for the ultraviolet to visible absorption spectrum are as follows. AA, A, and B are practically no problem levels. [Evaluation criteria] AA: The absorbance at a wavelength of 400 nm is 0.8 or more A: The absorbance at a wavelength of 400 nm is 0.4 or more and less than 0.8 B: The absorbance at a wavelength of 400 nm is 0.2 or more and less than 0.4 C: The absorbance at a wavelength of 400 nm is less than 0.2
  • C-1 TINUVIN 326 (manufactured by BASF Japan, benzotriazole)
  • C-2 TINUVIN 400 (manufactured by BASF Japan, triazine system)
  • C-3 Adekastab 1413 (manufactured by ADEKA Co., Ltd., benzophenone type)
  • D The coloring materials (D) used in the examples are shown below.
  • D-1 C.I. I. Pigment Blue PB15:6
  • D-2 C.I. I. Solvent Red SR52
  • D-3 C.I. I. Pigment Yellow PY147
  • the near-infrared absorbent (E) used in the examples is shown below.
  • thermoplastic resins used in the examples are shown below.
  • G-1) Polyester MA-2101M polyyester, manufactured by Unitika Ltd., crystalline resin, melting point 264°C, MFR 45g/10min (280°C/2.16kg)
  • G-2) Iupilon S-3000 polycarbonate resin, manufactured by Mitsubishi Engineering-Plastics, amorphous resin, glass transition temperature 145°C, M
  • Liquid resins used in the examples are shown below.
  • H-1 Uniol D-1200 (manufactured by NOF Corporation, polyalkylene glycol resin, polypropylene glycol resin, number average molecular weight 1200, viscosity 200 mPa s)
  • H-2 PEG-400 (manufactured by Sanyo Chemical Industries, polyalkylene glycol resin, polypropylene glycol resin, number average molecular weight 400, viscosity 90 mPa s)
  • H-3 Uniol D-400 (manufactured by NOF Corporation, polyalkylene glycol resin, polypropylene glycol resin, number average molecular weight 400, viscosity 100 mPa s)
  • H-4 Adekasizer RS-107 (manufactured by ADEKA Co., Ltd., ether ester resin, adipate ether ester resin, number average molecular weight 430, viscosity 20 mPa s
  • the polymerization solution was sampled and the non-volatile content was measured, and it was confirmed that the polymerization conversion rate was 98% or more in terms of the non-volatile content.
  • 20 parts of PGMAc, 21.2 parts of an ethylenically unsaturated monomer (b-5) as a second block monomer, and 27 parts of an ethylenically unsaturated monomer (b-9) aqueous solution (non-volatile 38%) was added, and the mixture was stirred while maintaining the temperature at 110°C under nitrogen atmosphere to continue the reaction.
  • the polymerization solution was sampled and the non-volatile content was measured to confirm that the polymerization conversion rate of the second block was 98% or more in terms of the non-volatile content, and the reaction solution was cooled to room temperature to stop the polymerization. bottom.
  • PGMAc was added to the previously synthesized block copolymer solution so that the non-volatile content was 40% by mass.
  • a resin-type dispersant solution having an amine value per nonvolatile content of 50 mgKOH/g, a quaternary ammonium salt value of 20 mgKOH/g, a weight average molecular weight (Mw) of 9,800, and a nonvolatile content of 40% by mass was obtained. rice field.
  • liquid resin (H-4) as the non-volatile content of this resin-type dispersant solution is added, heated to 100° C. and reduced in pressure to distill off PGMAc and water, thereby obtaining this resin-type dispersant solution.
  • Example 2-1 ⁇ Production of masterbatch> 2 parts of the UV absorbing dye 1 and 98 parts of the polyolefin resin (F-1) were fed from the same supply port into a twin-screw extruder with a screw diameter of 30 mm (manufactured by Japan Steel Works, Ltd.) and melt-mixed at 240 ° C. After kneading, the mixture was cut into pellets using a pelletizer to prepare a masterbatch (K-1).
  • Example 2-2 to 2-30 Comparative Examples 2-1 to 2-10) Films (X-2) to (X-30) and (XX-1) to (XX-10) having a thickness of 250 ⁇ m were formed using the materials shown in Table 3 in the same manner as in Example 2-1. .
  • AA Light transmittance at wavelengths of 400 to 420 nm is less than 1% over the entire region: Very good A: Light transmittance at wavelengths of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good B: Wavelengths of 400 to 420 nm Light transmittance of 5% or more and less than 10% over the entire region: Practical range C: Light transmittance of 400 to 420 nm wavelength of 10% or more over the entire region: Not practical
  • Example 2-31 ⁇ Production of masterbatch> 2 parts of the ultraviolet absorbing dye 1 and 98 parts of the polyester (G-1) are fed from the same supply port into a twin-screw extruder with a screw diameter of 30 mm (manufactured by Japan Steel Works, Ltd.) and melt-mixed at 240 ° C. After kneading, the material was cut into pellets using a pelletizer to produce a masterbatch (K-31).
  • Examples 2-32 to 2-60, Comparative Examples 2-11 to 2-20 Films (X-32) to (X-60) and (XX-11) to (XX-20) having a thickness of 250 ⁇ m were prepared using the materials listed in Table 4-1 in the same manner as in Example 2-21. Molded.
  • Example 2-61 ⁇ Production of liquid masterbatch> A liquid masterbatch (K-61) was produced by kneading 10 parts of the ultraviolet absorber 1 and 90 parts of the liquid resin (H-1) with a roll.
  • ⁇ Film molding> 0.5 parts of the obtained liquid masterbatch (K-61) is mixed with 99.5 parts of the thermoplastic resin (G-1) of the diluted resin, and a T-die molding machine (manufactured by Toyo Seiki Co., Ltd.) is used. was melt-mixed at a temperature of 300° C. to form a film (X-61) having a thickness of 250 ⁇ m.
  • Examples 2-62 to 2-90 In the same manner as in Example 2-61, films (X-62) to (X-90) with a thickness of 250 ⁇ m were formed using the materials listed in Table 4-2.
  • Example 2-91 ⁇ Production of liquid masterbatch> 10 parts of the ultraviolet absorbing dye 1, 20 parts of the resin type dispersant (J-1), and 70 parts of the liquid resin (H-1) are dispersed in a bead mill to obtain a liquid masterbatch (K-91). manufactured.
  • ⁇ Film molding> 0.5 parts of the obtained liquid masterbatch (K-91) is mixed with 99.5 parts of the thermoplastic resin (G-1) of the diluted resin, and a T-die molding machine (manufactured by Toyo Seiki Co., Ltd.) is used. was melt-mixed at a temperature of 300° C. to form a film (X-91) having a thickness of 250 ⁇ m.
  • Example 292 to 2-120 Films (X-92) to (X-120) with a thickness of 250 ⁇ m were formed using the materials shown in Table 4-2 in the same manner as in Example 2-91.
  • plasticizer dispersion (K-121) was prepared by bead-dispersing 10 parts of UV absorber 1 and 90 parts of plasticizer (I-1).
  • Example 2122 to 2-150 Films (X-122) to (X-150) with a thickness of 250 ⁇ m were formed using the materials shown in Table 4-3 in the same manner as in Example 2-121.
  • ⁇ Film molding> 0.5 parts of the obtained plasticizer dispersion (K-151) is mixed with 99.5 parts of the thermoplastic resin (G-1) of the diluted resin, and a T-die molding machine (manufactured by Toyo Seiki Co., Ltd.) were melt-mixed at a temperature of 280° C. to form a film (X-151) having a thickness of 250 ⁇ m.
  • Example 2152 to 2-180 Films (X-152) to (X-180) with a thickness of 250 ⁇ m were formed using the materials shown in Table 4-3 in the same manner as in Example 2-151.
  • AA Light transmittance at wavelengths of 400 to 420 nm is less than 1% over the entire region: Very good A: Light transmittance at wavelengths of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good B: Wavelengths of 400 to 420 nm Light transmittance of 5% or more and less than 10% over the entire region: Practical range C: Light transmittance of 400 to 420 nm wavelength of 10% or more over the entire region: Not practical
  • AAA, AA, A, and B are practically acceptable levels.
  • Evaluation criteria AAA: less than 0.2: very good AA: 0.2 or more and less than 0.5: very good A: 0.5 or more and less than 2: good B: 2 or more and less than 5: good C: 5 or more: not practical
  • the molded articles of the embodiments of the present invention have high UV absorption per unit weight and high light resistance in the visible light short wavelength region of 400 to 420 nm.
  • the transparency of the film is high and the haze is low because the addition of a small amount reaches the practical range.
  • Example 3-1 ⁇ Production of masterbatch> 2 parts of the ultraviolet absorbing dye 1 and 98 parts of the thermoplastic resin (G-1) are put into a twin-screw extruder with a screw diameter of 30 mm (manufactured by Japan Steel Works, Ltd.) from the same supply port, and melted at 300 ° C. After kneading, the mixture was cut into pellets using a pelletizer to produce a masterbatch (K-31).
  • Examples 3-2 to 3-150, Comparative Examples 3-1 to 3-10) In the same manner as in Example 3-1, films (Y-2) to (Y-150), (YY-1) to (YY) having a thickness of 250 ⁇ m were prepared using the materials listed in Tables 4-1 to 4-3. -10) was molded.
  • AA Light transmittance at wavelengths of 400 to 420 nm is less than 1% over the entire region: Very good A: Light transmittance at wavelengths of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good B: Wavelengths of 400 to 420 nm Light transmittance of 5% or more and less than 10% over the entire region: Practical range C: Light transmittance of 400 to 420 nm wavelength of 10% or more over the entire region: Not practical
  • the molded article using the ultraviolet absorber of the embodiment of the present invention has a small rate of change in ultraviolet absorption due to residence time during melt mixing during film molding. Therefore. It was confirmed that it possessed good heat resistance.
  • Example 4-1 ⁇ Production of UV region absorbing masterbatch> 1 part of UV absorber 3, 1 part of UV absorber C-1, and 98 parts of UV absorber polyester (G-1) are fed from the same supply port into a twin-screw extruder with a screw diameter of 30 mm (Nippon Steel Co., Ltd. (manufactured by the company), melted and kneaded at 240° C., and cut into pellets using a pelletizer to produce a masterbatch (K-121).
  • Examples 4-2 to 4-3) Films (Z-2) to (Z-3) having a thickness of 250 ⁇ m were formed using the materials shown in Table 6-1 in the same manner as in Example 4-1.
  • the transmittance of the obtained film was measured using an ultraviolet-visible-near-infrared spectrophotometer (manufactured by Shimadzu Corporation) to evaluate whether or not the following conditions were satisfied. A and B are practically no problem levels.
  • evaluation criteria A: Light transmittance at a wavelength of 400 to 420 nm is less than 1% over the entire region: Very good B: Light transmittance at a wavelength of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good C: A wavelength of 400 to 420 nm Light transmittance of 5% or more over the entire area is not practical
  • Heat resistance was evaluated in the same manner as in Example 3. Evaluation criteria are as follows. A and B are practically no problem levels. [Evaluation criteria] A: Difference in light transmittance at wavelength 400 to 420 nm is less than 1%: Good B: Difference in light transmittance at wavelength 400 to 420 nm is 1% or more and less than 5%: Practical range C: Light transmittance at wavelength 400 to 420 nm difference is 5% or more: impractical
  • Example 4-4 ⁇ Production of ultraviolet/visible light absorption masterbatch> 1 part of UV absorber 3, 1 part of colorant D-1, 1 part of colorant D-2, 1 part of colorant D-3, 96 parts of UV absorber polyester (G-1), the same It is put into a twin-screw extruder with a screw diameter of 30 mm (manufactured by The Japan Steel Works, Ltd.) from the supply port, melted and kneaded at 240 ° C., and then cut into pellets using a pelletizer to masterbatch (K-124). manufactured.
  • Example 4-5 to 4-6 Films (Z-5) to (Z-6) with a thickness of 250 ⁇ m were formed using the materials shown in Table 6-1 in the same manner as in Example 4-4.
  • the transmittance of the obtained film was measured using an ultraviolet-visible-near-infrared spectrophotometer (manufactured by Shimadzu Corporation) to evaluate whether or not the following conditions were satisfied. A and B are practically no problem levels.
  • evaluation criteria A: Light transmittance at wavelengths of 400 to 650 nm is less than 1% over the entire region: Good B: Light transmittance at wavelengths from 400 to 650 nm is 1% or more and less than 5%: Practical range C: Light at wavelengths from 400 to 650 nm Transmittance of 5% or more: Not practical
  • Example 4--7 ⁇ Production of UV/Near Infrared Region Masterbatch> 1 part of UV absorber 3, 1 part of near-infrared collecting dye E-1, and 98 parts of UV absorber polyester (G-1) are fed from the same supply port into a twin-screw extruder with a screw diameter of 30 mm (Co., Ltd. Japan Steel Works), melted and kneaded at 240° C., and cut into pellets using a pelletizer to produce a masterbatch (K-127).
  • Example 4-8 to 4-11 Films (Z-8) to (Z-11) having a thickness of 250 ⁇ m were formed using the materials shown in Table 6-1 in the same manner as in Example 4-7.
  • the transmittance of the obtained film was measured using an ultraviolet-visible-near-infrared spectrophotometer (manufactured by Shimadzu Corporation) to evaluate whether or not the following conditions were satisfied.
  • a and B are practically no problem levels.
  • Example 4-12 ⁇ Production of ultraviolet/near-infrared absorption masterbatch> 1 part of the UV absorber 3, 1 part of the UV absorber C-1, 1 part of the near-infrared collecting dye E-1, and 97 parts of the UV absorber polyester (G-1) are fed from the same supply port to the screw. It was put into a twin-screw extruder with a diameter of 30 mm (manufactured by The Japan Steel Works, Ltd.), melted and kneaded at 240° C., and cut into pellets using a pelletizer to produce a masterbatch (K-132).
  • Example 4-13 to 4-16 Films (Z-13) to (Z-16) having a thickness of 250 ⁇ m were formed using the materials shown in Table 6-1 in the same manner as in Example 4-12.
  • the transmittance of the obtained film was measured using an ultraviolet-visible-near-infrared spectrophotometer (manufactured by Shimadzu Corporation) to evaluate whether or not the following conditions were satisfied.
  • a and B are practically no problem levels.
  • Examples 5-2 to 5-20, Comparative Examples 5-1 to 5-10) As shown in Table 7, preparations were made in the same manner as in Example 5-1 to obtain paints of Examples 5-2 to 5-30 and Comparative Examples 5-1 to 5-10, respectively.
  • the obtained paint was applied to a glass substrate having a thickness of 1000 ⁇ m using a bar coater so that the dry film thickness was 10 ⁇ m, and dried at 100° C. for 2 minutes to form a coating film.
  • AA Light transmittance at wavelengths of 400 to 420 nm is less than 1% over the entire region: Very good A: Light transmittance at wavelengths of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good B: Wavelengths of 400 to 420 nm Light transmittance of 5% or more and less than 10% over the entire region: Practical range C: Light transmittance of 400 to 420 nm wavelength of 10% or more over the entire region: Not practical
  • the coating film using the UV absorber of the embodiment of the present invention has high UV absorption in the visible light short wavelength region of 400 to 420 nm and high light resistance. It was found that the transparency of the coated material is not impaired because it reaches the practical range with the addition of a small amount.
  • Photocurable composition (Example 6-1) In the following composition, each raw material was stirred and mixed to prepare a photocurable composition.
  • UV absorber 1 1.0 parts Photopolymerizable compound (polyfunctional acrylate "KAYARAD DPHA” manufactured by Nippon Kayaku Co., Ltd.) 18.0 parts Photopolymerization initiator (IGM ResinBV "Omnirad 184”) 1.0 parts Propylene glycol monomethyl ether 80.0 parts
  • Examples 6-2 to 6-30, Comparative Examples 6-1 to 6-10) As shown in Table 8, preparations were made in the same manner as in Example 6-1 to obtain photocurable compositions of Examples 6-2 to 6-30 and Comparative Examples 6-1 to 6-10, respectively.
  • the above photocurable composition was applied to a glass substrate having a thickness of 1 mm using a bar coater so that the dry film thickness was 6 ⁇ m.
  • the resulting coating layer was dried at 100° C. for 1 minute and then cured by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp to form a coating.
  • AA Light transmittance at wavelengths of 400 to 420 nm is less than 1% over the entire region: Very good A: Light transmittance at wavelengths of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good B: Wavelengths of 400 to 420 nm Light transmittance of 5% or more and less than 10% over the entire region: Practical range C: Light transmittance of 400 to 420 nm wavelength of 10% or more over the entire region: Not practical
  • the coating film using the UV absorber of the embodiment of the present invention has high UV absorption in the visible light short wavelength region of 400 to 420 nm and high light resistance. It was found that the transparency of the coated material is not impaired because it reaches the practical range with the addition of a small amount. It was also found to have good scratch resistance.
  • ⁇ Adhesive> (Production example of adhesive resin (L-1)) 96.0 parts of n-butyl acrylate and 4.0 parts of 2-hydroxyethyl acrylate under a nitrogen atmosphere using a reactor equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer and dropping tube. 50% of the total amount, 0.2 parts of 2,2'-azobisisobutylnitrile as a polymerization initiator, and 150 parts of ethyl acetate as a solvent are charged into a reactor, and the remaining 50% of the total amount An appropriate amount of ethyl acetate was charged into the dropping tank.
  • TDI-TMP tolylene diisocyanate trimethylolpropane adduct
  • this pressure-sensitive adhesive was applied onto a polyethylene terephthalate release film having a thickness of 38 ⁇ m so that the thickness after drying was 50 ⁇ m, and dried in a hot air oven at 100° C. for 2 minutes. Then, a 25 ⁇ m polyethylene terephthalate film was adhered to the pressure-sensitive adhesive layer side, and aged in this state at room temperature for 7 days to obtain a pressure-sensitive adhesive sheet.
  • Example 7-2 to 7-30 Comparative Examples 7-1 to 7-10
  • Table 9 pressure-sensitive adhesive sheets of Examples 7-2 to 7-30 and Comparative Examples 7-1 to 7-10 were obtained by adjusting in the same manner as in Example 7-1.
  • the obtained pressure-sensitive adhesive sheet was prepared in a size of 25 mm in width and 150 mm in length. In an atmosphere of 23° C. and a relative humidity of 50%, the peelable film was removed from the adhesive sheet, and the exposed adhesive layer was attached to a glass plate and crimped once with a 2 kg roll. After being left for 24 hours, the adhesive strength was measured in a 180° peel test in which a tensile tester was used to peel off at a speed of 300 mm/min in the 180° direction, and evaluation was performed based on the following evaluation criteria (JIS Z0237: 2000). ). A is a practically acceptable level. [Evaluation criteria] A: The adhesive strength is 10 N or more, which is good. C: Adhesive strength is less than 10 N, not practical.
  • the obtained pressure-sensitive adhesive sheet was prepared in a size of 25 mm in width and 150 mm in length.
  • the release sheet was peeled off from the adhesive sheet, and an adhesive layer was attached to a polished stainless steel plate having a width of 30 mm and a length of 150 mm.
  • a load of 1 kg was applied in an atmosphere of 40° C., and the holding force was measured by leaving it for 70,000 seconds.
  • the length by which the upper end of the adhesive sheet pasting surface shifted downward was measured. A is a practically acceptable level.
  • A The deviated length of the adhesive sheet is less than 0.5 mm. Good.
  • C The length of deviation of the adhesive sheet is 0.5 mm or more. Not practical.
  • AA Light transmittance at wavelengths of 400 to 420 nm is less than 1% over the entire region: Very good A: Light transmittance at wavelengths of 400 to 420 nm is 1% or more and less than 5% over the entire region: Good B: Wavelengths of 400 to 420 nm Light transmittance of 5% or more and less than 10% over the entire region: Practical range C: Light transmittance of 400 to 420 nm wavelength of 10% or more over the entire region: Not practical
  • the coating film using the ultraviolet absorber of the embodiment of the present invention has high ultraviolet absorption in the visible light short wavelength region of 400 to 420 nm and high light resistance. It was found that the transparency of the pressure-sensitive adhesive sheet is not impaired because it can be practically used by adding a small amount. It was also found to have good adhesion and holding power.

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Abstract

Absorbeur d'UV contenant : au moins un type de colorant absorbant les UV choisi dans le groupe constitué par les composés représentés par les formules générales (1)- (3) ; et un constituant métallique contenant au moins un type d'atome de métal choisi dans le groupe constitué par Na, Mg, Al, K, Ca et Fe, la teneur des constituants métalliques mentionnés ci-dessus étant de 0,1 à 50 000 ppm de l'absorbeur d'UV.
PCT/JP2022/027201 2021-07-14 2022-07-11 Absorbeur d'uv et son procédé de fabrication, composition, corps moulé et film de revêtement WO2023286725A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
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GB1107143A (en) * 1966-02-01 1968-03-20 Ciba Ltd Di-(hydroxynaphthyl)-triazines and processes for their manufacture and use
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GB1107143A (en) * 1966-02-01 1968-03-20 Ciba Ltd Di-(hydroxynaphthyl)-triazines and processes for their manufacture and use
JPH09176135A (ja) * 1995-12-19 1997-07-08 Givaudan Roure Internatl Sa 遮光剤として有用な化合物
EP1298126A1 (fr) * 2001-09-27 2003-04-02 Cytec Technology Corp. Nouveaux triazines comme absorbeurs d'UV décalés vers le rouge
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WO2021132247A1 (fr) * 2019-12-24 2021-07-01 東洋インキＳｃホールディングス株式会社 Composition de résine et article moulé

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