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WO2025154810A1 - Absorbeur d'ultraviolets, composition de résine, pastilles, article moulé, composé et procédé de production de composé - Google Patents

Absorbeur d'ultraviolets, composition de résine, pastilles, article moulé, composé et procédé de production de composé

Info

Publication number
WO2025154810A1
WO2025154810A1 PCT/JP2025/001436 JP2025001436W WO2025154810A1 WO 2025154810 A1 WO2025154810 A1 WO 2025154810A1 JP 2025001436 W JP2025001436 W JP 2025001436W WO 2025154810 A1 WO2025154810 A1 WO 2025154810A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound represented
resin composition
ultraviolet absorber
less
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/001436
Other languages
English (en)
Japanese (ja)
Inventor
大 小黒
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Engineering Plastics Corp
Original Assignee
Mitsubishi Engineering Plastics Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Engineering Plastics Corp filed Critical Mitsubishi Engineering Plastics Corp
Publication of WO2025154810A1 publication Critical patent/WO2025154810A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • 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
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • 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 absorbent, a resin composition, a pellet, a molded product, a compound, and a method for producing the compound.
  • an ultraviolet absorber that can sufficiently cut (reduce transmittance) blue light (hereinafter sometimes referred to as "blue light”) with a wavelength of 400 nm or more in the obtained molded product when blended with resin. Even if the ultraviolet absorber can sufficiently cut blue light of 400 nm or more, when blended with a thermoplastic resin and molded using a mold such as injection molding, or when extrusion molding of a sheet or film with a large surface area per weight of the resin composition, mold deposits derived from the highly volatile ultraviolet absorber can become an issue.
  • An ultraviolet absorber containing a compound represented by formula (1) and/or a compound represented by formula (2).
  • each R is independently a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom and/or a hydroxyl group, a halogen atom, or a hydroxyl group.
  • Each n is independently an integer of 0 to 4.
  • An ultraviolet absorber comprising a compound represented by formula (1).
  • ⁇ 4> The ultraviolet absorber according to ⁇ 1> or ⁇ 2>, wherein, in formula (1), at least one of R is a methyl group.
  • An ultraviolet absorber comprising a compound represented by formula (3) or a compound represented by formula (4).
  • t-Bu represents a tert-butyl group.
  • An ultraviolet absorber comprising a compound represented by formula (3) and a compound represented by formula (4).
  • t-Bu represents a tert-butyl group.
  • a resin composition comprising a thermoplastic resin and the ultraviolet absorber according to any one of ⁇ 1> to ⁇ 6>.
  • n's each independently represent an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0.
  • the total number of R in one molecule of the compound represented by formula (2) is preferably an integer of 0 to 2, more preferably 0 or 2, and even more preferably 0.
  • n the number of R bonded to one ring, i.e., n, in R, which is a hydrocarbon group having 4 or more carbon atoms, is 1 or less.
  • n the number of R bonded to one ring, i.e., n, in R, which is a hydrocarbon group having 4 or more carbon atoms, is 1 or less.
  • the ultraviolet absorber of the present embodiment preferably does not contain the compounds shown below. By not containing the compounds shown below, the effect of reducing the transmittance of blue light having a wavelength of 400 nm or more tends to be more effectively exerted.
  • t-Bu represents a tert-butyl group.
  • the UV absorbent of this embodiment can be produced by a known method.
  • This embodiment also discloses a method for producing a compound represented by formula (1-1), which comprises heating a compound represented by formula (5-1) and a sulfidizing agent in the presence of an organic solvent.
  • R 1 's are each independently a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, or a hydroxyl group; n is an integer of 0 to 4; and Hr is a halogen atom.
  • R 1 's are each independently a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, or a hydroxyl group.
  • Each n is independently an integer of 0 to 4.
  • each R 1 is independently a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, or a hydroxyl group, and more preferably an unsubstituted hydrocarbon group having 1 to 12 carbon atoms.
  • the hydrocarbon group is preferably an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, more preferably an alkyl group.
  • the alkyl group is preferably a linear or branched alkyl group.
  • the number of carbon atoms in the hydrocarbon group is preferably 1 or more, more preferably 2 or more, even more preferably 3 or more, and even more preferably 4 or more, and is preferably 10 or less, more preferably 8 or less, even more preferably 6 or less, even more preferably 5 or less, and even more preferably 4 or less.
  • the halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a fluorine atom or a chlorine atom, and even more preferably a chlorine atom.
  • each n is independently an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 2.
  • R 1 and n in formula (1-1) each independently have the same definition as R 1 and n in formula (5-1), and the preferred ranges are also the same.
  • the preferred range of the formula (1-1) is the same as the preferred range of the compound represented by the formula (1) (excluding R1 ).
  • the compound represented by formula (5-1) and a sulfidizing agent are heated in the presence of an organic solvent.
  • the sulfidizing agent may be any agent capable of introducing a sulfide bond into the compound represented by formula (5-1) to synthesize the compound represented by formula (1-1), and examples of such agents include alkaline (earth) metal sulfides.
  • alkali (earth) metal sulfide examples include mercaptoalkyl acid alkali (earth) metal salts, lithium sulfide, sodium sulfide, potassium sulfide, rubidium sulfide, cesium sulfide, calcium sulfide, and mixtures of two or more of these.
  • mercaptoalkyl acid alkali (earth) metal salts, lithium sulfide and/or sodium sulfide are preferably used.
  • alkaline (earth) metal sulfides can be used in the form of anhydrides, but are preferably used as hydrates or aqueous mixtures from the viewpoints of availability and cost, and alkaline (earth) metal sulfides in the form of hydrates can be particularly preferably used.
  • the aqueous mixture refers to an aqueous solution, or a mixture of an aqueous solution and a solid component, or a mixture of water and a solid component.
  • the use of a hydrate or an aqueous mixture as a sulfidizing agent tends to make it more miscible with organic solvents, and therefore can be exemplified as a preferred form from the viewpoint of reaction efficiency.
  • alkali (earth) metal hydrides and alkali (earth) metal carbonates are preferably used, among which sodium hydride and calcium carbonate are preferably used, and sodium hydride is particularly preferably used.
  • Preferred examples of the mercaptoalkyl acid alkali (earth) metal salt include disodium mercaptopropionate, calcium mercaptopropionate, and potassium thioacetate, with potassium thioacetate and/or disodium mercaptopropionate being preferred.
  • the amount of the sulfidizing agent used is preferably 0.5 mol or more, more preferably 1 mol or more, and even more preferably 2 mol or more, and is preferably 20 mol or less, more preferably 10 mol or less, and even more preferably 5 mol or less, relative to 1 mol of the compound represented by formula (5-1).
  • only one type of sulfidizing agent may be contained, or two or more types may be contained. When two or more types are contained, it is preferable that the total amount is in the above range.
  • organic solvents include nitrogen-containing polar solvents such as N-methyl-2-pyrrolidone (NMP), N-methylcaprolactam, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), 1,3-dimethyl-2-imidazolidinone (DMI), hexamethylphosphoramide, and tetramethylurea; sulfoxide/sulfone-based solvents such as dimethyl sulfoxide (DMSO), dimethyl sulfone, diphenyl sulfone, and sulfolane; nitrile-based solvents such as benzonitrile; diaryl ethers such as diphenyl ether; ketones such as acetone, benzophenone, and acetophenone; aromatic hydrocarbons such as benzene, toluene, and xylene; and mixtures thereof.
  • nitrogen-containing polar solvents are preferred, and N,N-dimethyl
  • a surfactant may be added. Addition of a surfactant may improve the affinity between the sulfidizing agent and the compound represented by formula (5-1) in the solvent, thereby improving the yield.
  • Specific examples of the surfactant include quaternary ammonium salts, phosphonium salts, crown ethers, (poly)alkylene glycols, cyclodextrins, alkyl fatty acid salts, and alkyl sulfates.
  • the sulfidation reaction is carried out by heating.
  • the reaction temperature is preferably 40° C. or higher, more preferably 60° C. or higher, even more preferably 80° C. or higher, even more preferably 100° C. or higher, even more preferably 120° C. or higher, and preferably 250° C. or lower, more preferably 225° C. or lower, even more preferably 200° C. or lower, even more preferably 175° C. or lower, and even more preferably 150° C. or lower.
  • R 1 and n in formula (2-1) each independently have the same definition as R 1 and n in formula (5-2), and the preferred ranges are also the same.
  • the preferred range of the compound represented by formula (2-1) is the same as the preferred range of the compound represented by formula (2) (excluding R1 ), and the compound represented by formula (4) is more preferred.
  • the hydrocarbon group is preferably an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, more preferably an alkyl group.
  • the alkyl group is preferably a linear or branched alkyl group.
  • R 1 and n in formula (2-1) each independently have the same definition as R 1 and n in formula (5-2), and the preferred ranges are also the same.
  • the preferred range of the compound represented by formula (2-1) is the same as the preferred range of the compound represented by formula (2) (excluding R1 ).
  • Methods for purifying the compounds obtained in the present invention include purification methods such as crystallization and column chromatography.
  • organic solvents used in the present crystallization purification include alcohols such as isopropyl alcohol, ester solvents such as ethyl acetate and butyl acetate, nitrogen-containing polar solvents such as N-methyl-2-pyrrolidone (NMP), N-methylcaprolactam, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), 1,3-dimethyl-2-imidazolidinone (DMI), hexamethylphosphoramide, and tetramethylurea, sulfoxide-sulfone solvents such as dimethyl sulfoxide (DMSO), dimethyl sulfone, diphenyl sulfone, and sulfolane, nitrile solvents such as benzonitrile, diaryl ethers such as diphenyl ether, ketones such as
  • the use of the ultraviolet absorbent of this embodiment is not particularly limited, and it can be used widely for the purposes in which ultraviolet absorbents are generally used.
  • the ultraviolet absorbent of the present embodiment is blended into materials such as thermoplastic resins and thermosetting resins, and is also widely used in adhesives, cosmetics, coating agents, paints, inks, and the like.
  • the ultraviolet absorbent of the present embodiment is preferably used as an ultraviolet absorbent for thermoplastic resins because it is unlikely to cause mold deposits when blended with a thermoplastic resin and molded with a die.
  • the resin composition of the present embodiment includes a thermoplastic resin and the ultraviolet absorbent of the present embodiment.
  • a molded article formed from such a resin composition has excellent ultraviolet absorption properties and generates little mold deposits derived from the ultraviolet absorbent during molding.
  • thermoplastic resin contained in the resin composition of this embodiment is not particularly limited in type, and examples thereof include polycarbonate resin, polyphenylene ether resin, polystyrene resin, polyamide resin alloy, thermoplastic polyester resin, acrylic resin, polyacetal resin, polylactic acid resin, polyolefin resin, etc., and preferably contains at least one of acrylic resin, amorphous polyester resin, and polycarbonate resin, more preferably contains at least one of acrylic resin and polycarbonate resin, and even more preferably contains polycarbonate resin.
  • polycarbonate resin and acrylic resin it is also preferable to contain polycarbonate resin and acrylic resin, as this provides good transparency and hardness. In this case, it is preferable to contain 10 to 100 parts by mass of acrylic resin per 100 parts by mass of polycarbonate resin.
  • R is an organic group, preferably a hydrocarbon group, more preferably an aliphatic group, an aromatic group, or both an aliphatic group and an aromatic group, and further has a straight-chain structure or a branched structure
  • acrylic resin examples include methyl methacrylate resin (PMMA), rubber-reinforced methyl methacrylate resin, methyl methacrylate/acrylonitrile/butadiene/styrene copolymer resin, and methyl methacrylate/styrene copolymer resin.
  • PMMA methyl methacrylate resin
  • rubber-reinforced methyl methacrylate resin methyl methacrylate/acrylonitrile/butadiene/styrene copolymer resin
  • methyl methacrylate/styrene copolymer resin examples include methyl methacrylate/styrene copolymer resin.
  • the description in paragraphs 0037 to 0069 of JP 2018-87268 A can be referred to, and the contents thereof are incorporated herein.
  • the acrylic resin having aromatic (meth)acrylate units described in the above publication is used for the polycarbonate resin
  • a polycarbonate resin composition having excellent surface hardness, transparency, particularly transparency during high-speed injection molding, and also excellent retention heat stability, and a molded article obtained by molding this polycarbonate resin composition can be obtained.
  • the acrylic resin generally, 50% by mass or more of the structural units are derived from (meth)acrylate, and more preferably 90% by mass or more is derived from (meth)acrylate, because this provides high total light transmittance and excellent transparency.
  • the content of the ultraviolet absorber in the resin composition of this embodiment is preferably 0.0001 parts by mass or more, more preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, even more preferably 0.01 parts by mass or more, even more preferably 0.03 parts by mass or more, even more preferably 0.05 parts by mass or more, and preferably 3 parts by mass or less, more preferably 1 part by mass or less, even more preferably 0.8 parts by mass or less, even more preferably 0.7 parts by mass or less, even more preferably 0.6 parts by mass or less, even more preferably 0.5 parts by mass or less, and even more preferably 0.4 parts by mass or less.
  • the compound represented by formula (3) when used as an ultraviolet absorber, the compound is preferably blended in an amount of 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.02 parts by mass or more, even more preferably 0.03 parts by mass or more, particularly preferably more than 0.05 parts by mass, preferably 1 part by mass or less, more preferably 0.5 parts by mass or less, even more preferably 0.4 parts by mass or less, even more preferably less than 0.3 parts by mass, even more preferably less than 0.2 parts by mass, and especially preferably less than 0.1 parts by mass, even if the compound is blended in an amount as small as 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.4 parts by mass or less, even more preferably less than 0.3 parts by mass, even more preferably less than 0.2 parts by mass, and especially preferably less than 0.1 parts by mass, it is possible to sufficiently cut blue light having a wavelength of 400 nm or more, and even more 0.05 parts
  • the YI is preferably 25 or less, more preferably 20 or less, even more preferably 15 or less, and especially preferably 5 or less.
  • the lower limit of the YI is not particularly specified, but 0.1 or more is practical.
  • the mass ratio of the compound represented by formula (3) to the compound represented by formula (4) is preferably 0.005 to 2.
  • the resin composition of the present embodiment may contain only one type of ultraviolet absorbent, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.
  • the resin composition of the present embodiment may contain other components as necessary, as long as the desired physical properties are not significantly impaired.
  • the other components include various resin additives and fillers.
  • resin additives include reactive compounds (e.g., epoxy compounds and/or oxetane compounds), stabilizers, release agents, colorants (dyes, pigments), antistatic agents, flame retardants, flame retardant assistants, anti-dripping agents, anti-fogging agents, anti-blocking agents, flow improvers, plasticizers, dispersants, and antibacterial agents.
  • One type of resin additive may be contained, or two or more types may be contained in any combination and ratio.
  • the content of the resin additive in the resin composition is preferably 0 to 3% by mass, and more preferably 0 to 1% by mass.
  • R 25 to R 29 each independently represent a hydrogen atom, an aryl group having 6 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms.
  • the phosphite stabilizer (CI) is not particularly limited as long as it is a phosphite compound having a spiro ring skeleton, but for example, one represented by the following formula (I) is preferred.
  • R 10A and R 10B each independently represent an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • the alkyl groups represented by R 10A and R 10B are preferably each independently a linear or branched alkyl group having 1 to 10 carbon atoms.
  • R 10A and R 10B are aryl groups, they are preferably aryl groups represented by any one of the following general formulae (I-1), (I-2), and (I-3).
  • R A represents an alkyl group having 1 to 10 carbon atoms.
  • R B represents an alkyl group having 1 to 10 carbon atoms.
  • C-I phosphite stabilizer
  • I-A bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite
  • phosphite stabilizer (C-I) are compounds represented by the following general formula (IB):
  • R 11 to R 18 are each preferably independently an alkyl group having 1 to 5 carbon atoms, more preferably a methyl group, and a to d are preferably 0.
  • the above phosphite stabilizers (C-I) may be used alone or in combination of two or more.
  • the phosphite stabilizer (C-II) is represented by the above general formula (II).
  • examples of the alkyl group represented by R 25 to R 29 include a methyl group, an ethyl group, a propyl group, a n-propyl group, a n-butyl group, a tert-butyl group, a hexyl group, and an octyl group.
  • tris(2,4-di-tert-butylphenyl)phosphite represented by the following structural formula (II-A) is particularly preferred.
  • C-II phosphite stabilizers
  • the content is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, even more preferably 0.01 parts by mass or more, even more preferably 0.05 parts by mass or more, even more preferably 0.1 parts by mass or more, and preferably 1 part by mass or less, more preferably 0.8 parts by mass or less, even more preferably 0.7 parts by mass or less, even more preferably 0.6 parts by mass or less, and even more preferably 0.5 parts by mass or less, relative to 100 parts by mass of a thermoplastic resin (preferably a polycarbonate resin).
  • a thermoplastic resin preferably a polycarbonate resin
  • the resin composition of the present embodiment may contain only one stabilizer (preferably a phosphorus-based stabilizer), or may contain two or more stabilizers. When two or more stabilizers are contained, the total amount is preferably within the above range.
  • the resin composition of the present embodiment preferably has excellent shielding properties for light with a wavelength of 400 nm (ultraviolet ray shielding properties).
  • the resin composition of this embodiment when molded into a test piece having a thickness of 3 mm, preferably has a light transmittance at a wavelength of 400 nm of 25% or less, more preferably 10% or less, more preferably 5% or less, even more preferably less than 3%, even more preferably less than 1%, and may even be 0%.
  • the resin composition of this embodiment satisfies the above-mentioned light transmittance at a wavelength of 400 nm, and when molded into a test piece with a thickness of 3 mm, the light transmittance at a wavelength of 420 nm is preferably 50% or less, more preferably 25% or less, even more preferably 10% or less, and even more preferably 5% or less, and may even be 0%.
  • an ultraviolet absorber containing a compound represented by formula (1), preferably formula (3) is suitably used.
  • the resin composition of this embodiment satisfies the above light transmittance, and when the resin composition of this embodiment is molded into a test piece having a thickness of 3 mm, the light transmittance at a wavelength of 420 nm is preferably more than 5%, more preferably more than 10%, even more preferably more than 25%, even more preferably more than 50%, and may even be more than 80%.
  • an ultraviolet absorber containing a compound represented by formula (2), preferably formula (4) is suitably used. The light transmittance is measured according to the description in the examples below.
  • the total light transmittance when the resin composition is molded into a test piece having a thickness of 3 mm is preferably 85% or more, more preferably 88% or more, even more preferably 89% or more, even more preferably 90% or more, and 100% or less.
  • the total light transmittance is the total light transmittance measured according to the measurement of light transmittance described in the Examples described later.
  • the molded article of this embodiment is formed from the resin composition or pellets of this embodiment.
  • the above-mentioned resin composition (for example, pellets) is molded into a molded article by various molding methods.
  • the shape of the molded article is not particularly limited and can be appropriately selected depending on the use and purpose of the molded article, and examples thereof include film-shaped, rod-shaped, cylindrical, annular, circular, elliptical, polygonal, irregular, hollow, frame-shaped, box-shaped, panel-shaped, and button-shaped articles.
  • the molded product of this embodiment is preferably used for eyewear parts, electrical and electronic equipment/components, office automation equipment/components, information terminal equipment/components, machine parts, home appliances, vehicle parts, building materials, various containers, leisure goods and sundries, lighting equipment, etc., and more specifically, is preferably used for transparent components such as eyeglass lenses, sunglasses, power covers, lighting lenses, lighting covers, and light-guiding components.
  • UV-3 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole)
  • DPPF 1,1'-bis(diphenylphosphino)ferrocene
  • Pd 2 (dba) 3 0.102 g, 0.111 mmol, 0.07 eq
  • dehydrated acetone (10 mL) were added, and argon bubbling was performed for 5 minutes, followed by heating and stirring at 130° C.
  • UV-2 intermediate 2-(2H-benzo[d][1,2,3]triazol-2-yl)-6-bromo-4-methylphenol
  • UV-2 intermediate 0.379 g, 1.25 mmol, 1.92 eq
  • potassium thioacetate 0.074 g, 0.648 mmol, 1.00 eq
  • DPPF 0.0428 g, 0.077 mmol, 0.12 eq
  • Pd 2 (dba) 3 0.0355 g, 0.039 mmol, 0.06 eq
  • dehydrated toluene 8 mL
  • dehydrated acetone 4 mL
  • UV-2 The mass spectrum of the obtained compound (UV-2) is as follows. MALDI-MS (pos.CHCA) [M/H]+m/z 481.148 [M/Na]+m/z 503.149 [M/K]+m/z 519.132
  • the molded article obtained above was used as a test piece, and the total light transmittance and the light transmittance at wavelengths of 400 nm and 420 nm were measured using a haze meter (NDH4000) manufactured by Nippon Denshoku Industries Co., Ltd., in accordance with ASTM-D1003, using a D65 light source, and the results were evaluated as follows.
  • NDH4000 haze meter manufactured by Nippon Denshoku Industries Co., Ltd., in accordance with ASTM-D1003, using a D65 light source, and the results were evaluated as follows.
  • the spectrophotometer used was a SE-2000 spectrophotometer manufactured by Nippon Denshoku Industries Co., Ltd. ⁇ Yellowness determination>> A: 5 or less B: More than 5 and less than 15 C: More than 15 and less than 20 D: More than 20
  • ⁇ Mold deposit> The mold deposits during the manufacture of the test pieces for measuring the light transmittance were visually inspected by five experts and evaluated as follows, and the results were determined by majority vote. A: No mold deposits were observed. B: A small amount of mold deposits were observed. C: Mold deposits were observed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne : un absorbeur d'ultraviolets qui peut couper suffisamment la lumière bleue ayant une longueur d'onde de 400 nm ou plus et supprimer efficacement les dépôts de moule ; une composition de résine ; des pastilles ; un article moulé ; un composé ; et un procédé de production du composé. L'absorbeur d'ultraviolets contient un composé représenté par la formule (1) et/ou un composé représenté par la formule (2). Dans la formule (1) et la formule (2), chaque R représente indépendamment un atome d'halogène, un groupe hydroxyle ou un groupe hydrocarboné en C1-12 qui peut être substitué par un atome d'halogène et/ou un groupe hydroxyle. Chaque n est indépendamment un nombre entier de 0 à 4.
PCT/JP2025/001436 2024-01-19 2025-01-17 Absorbeur d'ultraviolets, composition de résine, pastilles, article moulé, composé et procédé de production de composé Pending WO2025154810A1 (fr)

Applications Claiming Priority (2)

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JP2024-007058 2024-01-19
JP2024007058 2024-01-19

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CN1850809A (zh) * 2006-05-19 2006-10-25 中国科学院广州化学研究所 一种含硫的苯并三唑类化合物及其制备方法
JP2018522109A (ja) * 2015-07-07 2018-08-09 スリーエム イノベイティブ プロパティズ カンパニー イオン性添加剤を含むポリマーマトリックス
WO2020137819A1 (fr) * 2018-12-26 2020-07-02 ミヨシ油脂株式会社 Absorbant d'uv résistant à la lumière, résistant à la chaleur et durable

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CN1850809A (zh) * 2006-05-19 2006-10-25 中国科学院广州化学研究所 一种含硫的苯并三唑类化合物及其制备方法
JP2018522109A (ja) * 2015-07-07 2018-08-09 スリーエム イノベイティブ プロパティズ カンパニー イオン性添加剤を含むポリマーマトリックス
WO2020137819A1 (fr) * 2018-12-26 2020-07-02 ミヨシ油脂株式会社 Absorbant d'uv résistant à la lumière, résistant à la chaleur et durable

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