WO2024232439A1 - 組成物、塗料組成物、物品、組成物の製造方法、光安定剤モノマー成分および光安定剤重合体 - Google Patents

組成物、塗料組成物、物品、組成物の製造方法、光安定剤モノマー成分および光安定剤重合体 Download PDF

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WO2024232439A1
WO2024232439A1 PCT/JP2024/017486 JP2024017486W WO2024232439A1 WO 2024232439 A1 WO2024232439 A1 WO 2024232439A1 JP 2024017486 W JP2024017486 W JP 2024017486W WO 2024232439 A1 WO2024232439 A1 WO 2024232439A1
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carbon atoms
group
substituted
hydrocarbon group
general formula
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English (en)
French (fr)
Japanese (ja)
Inventor
和弥 石附
龍 片桐
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Adeka Corp
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Adeka Corp
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Priority to JP2025519477A priority Critical patent/JPWO2024232439A1/ja
Priority to EP24803547.9A priority patent/EP4711428A1/en
Priority to CN202480044974.1A priority patent/CN121443694A/zh
Publication of WO2024232439A1 publication Critical patent/WO2024232439A1/ja
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02Emulsion paints including aerosols
    • C09D5/022Emulsions, e.g. oil in water
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04Homopolymers or copolymers of esters
    • C09D133/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen

Definitions

  • the present invention relates to a composition, a coating composition, an article, a method for producing a composition, a light stabilizer monomer component, and a light stabilizer polymer, and more specifically to a composition, a coating composition, an article, a method for producing a composition, a light stabilizer monomer component, and a light stabilizer polymer that can form a dispersion with excellent stability under acidic conditions.
  • Patent Document 1 proposes an acrylic polymer with 2,2,6,6-tetramethyl-4-piperidyl methacrylate as a polymerization component as one such composition.
  • the object of the present invention is to provide a composition, a coating composition, an article, a method for producing a composition, a light stabilizer monomer component, and a light stabilizer polymer that can form a dispersion with excellent stability under acidic conditions.
  • the present invention provides a composition comprising a polymer obtained by polymerizing a monomer component containing a compound represented by the following general formula (1) and an aqueous dispersion medium.
  • the present invention also relates to a coating composition that contains a polymer obtained by polymerizing a monomer component that contains a compound represented by the above general formula (1).
  • the present invention relates to an article having a coating film obtained by applying the above-mentioned coating composition.
  • the present invention is a method for producing a composition, which includes a dispersion step of dispersing a polymer obtained by polymerizing a monomer component containing a compound represented by the above general formula (1) in an aqueous dispersion medium.
  • the present invention relates to a light stabilizer monomer component for use in a composition containing a light stabilizer polymer obtained by polymerizing a light stabilizer monomer component and an aqueous dispersion medium, the light stabilizer monomer component containing a compound represented by the above general formula (1).
  • the present invention relates to a light stabilizer polymer for use in a composition containing a light stabilizer polymer and an aqueous dispersion medium, the light stabilizer polymer being obtained by polymerizing a light stabilizer monomer component containing a compound represented by the above general formula (1).
  • the present invention provides a composition, a coating composition, an article, a method for producing a composition, a light stabilizer monomer component, and a light stabilizer polymer that can form a dispersion with excellent stability under acidic conditions.
  • composition of the present embodiment contains a polymer obtained by polymerizing a monomer component containing a compound represented by the following general formula (1), and an aqueous dispersion medium.
  • n1 represents 1 or 2.
  • Y 1 represents a single bond or a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms.
  • Z 1 represents a single bond or an oxygen atom.
  • R 3 , R 4 , R 5 , R 6 , R 7 , and R Each of 8 independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, and at least one of X 1 and R 1 is a group containing a vinyl group.
  • * represents a site for bonding to an oxygen atom
  • R2 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.
  • Z1 represents a single bond
  • Y1 represents a single bond means that Y1 has no atom, and the two carbon atoms connected to Y1 are directly bonded.
  • the composition of this embodiment can form a dispersion with excellent stability under acidic conditions. Furthermore, when the composition of this embodiment is used as a component of a coating composition, it can impart excellent light resistance to the coating film obtained by applying the coating composition.
  • composition of this embodiment can form a dispersion with excellent stability under acidic conditions. That is, 2,2,6,6-tetramethyl-4-piperidyl methacrylate has a piperidine ring, and the nitrogen atom on the piperidine ring is a secondary amine, so it is a basic compound. Therefore, when a dispersion in which a polymer obtained by polymerizing a monomer component containing this compound is dispersed in an aqueous dispersion medium is exposed to acidic conditions, the nitrogen atom on the piperidine ring in the polymer reacts with the acid to form a salt. The dispersion is prone to aggregation due to coagulation caused by the salt thus formed.
  • the nitrogen atom on the piperidine ring is a tertiary amine, and basicity is moderately suppressed. Due to this chemical structure, when a dispersion in which a polymer obtained by polymerizing a monomer component containing the compound represented by the above general formula (1) is dispersed in an aqueous dispersion medium is exposed to acidic conditions, salt formation is sufficiently suppressed. Furthermore, the compound represented by the above general formula (1) has a hydroxyl group and is moderately hydrophilic.
  • composition of the present embodiment contains a polymer, and this polymer is obtained by polymerizing a monomer component containing the compound represented by the above general formula (1).
  • Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 in general formula (1) and general formula (2) include substituted or unsubstituted monovalent aliphatic saturated hydrocarbon groups, substituted or unsubstituted monovalent aliphatic unsaturated hydrocarbon groups, and substituted or unsubstituted monovalent aromatic hydrocarbon groups.
  • examples of monovalent aliphatic saturated hydrocarbon groups include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, n-docosyl, and n-triacontyl, isopropyl, and isopropyl groups.
  • alkyl groups include branched alkyl groups such as butyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-amyl, 2-heptyl, tert-heptyl, 2-ethylhexyl, tert-octyl, isononyl, isodecyl, and 3,5,5-trimethylhexyl, and cyclic alkyl groups such as cyclopentyl, cyclohexyl, cyclooctyl, and adamantyl.
  • alkyl groups include branched alkyl groups such as butyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-amyl, 2-heptyl, tert-heptyl, 2-ethylhexyl, tert-octyl, isononyl, is
  • Examples of monovalent aliphatic unsaturated hydrocarbon groups include vinyl groups, 2-propenyl groups, 2-butenyl groups, 3-butenyl groups, 9-octadecenyl groups, and 9,12-octadecadienyl groups.
  • Examples of monovalent aromatic hydrocarbon groups include phenyl, naphthyl, biphenylyl, and anthracyl groups.
  • the substituent include halogen atoms such as fluorine atom, chlorine atom and bromine atom, alkoxy groups such as methoxy group, ethoxy group and tert-butyloxy group, trialkylsilyl groups such as trimethylsilyl group and triethylsilyl group, dialkylalkoxysilyl groups such as dimethylmethoxysilyl group, dimethylethoxysilyl group, diethylmethoxysilyl group and diethylethoxysilyl group, alkyldialkoxysilyl groups such as methyldimethoxysilyl group, methyldiethoxysilyl group, ethyldimethoxysilyl group and ethyldiethoxys
  • alkyl group examples include alkyl groups, trialkoxysilyl groups such as trimethoxysilyl group and triethoxysilyl group, trialkylsiloxy groups such as trimethylsiloxy group and triethylsiloxy group, dialkylalkoxysiloxy groups such as dimethylmethoxysiloxy group, dimethylethoxysiloxy group, diethylmethoxysiloxy group and diethylethoxysiloxy group, alkyldialkoxysiloxy groups such as methyldimethoxysiloxy group, methyldiethoxysiloxy group, ethyldimethoxysiloxy group and ethyldiethoxysiloxy group, and trialkoxysiloxy groups such as trimethoxysiloxy group and triethoxysiloxy group.
  • trialkoxysilyl groups such as trimethoxysilyl group and triethoxysilyl group
  • trialkylsiloxy groups such as trimethylsiloxy group and tri
  • Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms represented by X 1 in general formula (1) include the same as those exemplified as the substituted or unsubstituted monovalent hydrocarbon groups having 1 to 30 carbon atoms represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 .
  • examples of the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by X 1 in general formula (1) include divalent saturated hydrocarbon groups, divalent unsaturated hydrocarbon groups, etc.
  • examples of the divalent saturated hydrocarbon group include methylene group, ethylene group, propylene group, butylene group, hexylene group, octylene group, decylene group, dodecylene group, hexadecylene group, octadecylene group, eicosylene group, docosylene group, triacontylene group, linear alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, butane-1,1-diyl group, and hexane-1,1-diyl group, branched alkanediyl groups such as propane-2,2-diyl group, and cyclic alkanediyl
  • Examples of the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by Y 1 in general formula (1) include the same as those exemplified as the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by X 1 .
  • Z1 in general formula (1) is preferably an oxygen atom.
  • the hydrophilicity of the compound represented by general formula (1) is further improved, and the composition of the present embodiment can form a dispersion having excellent stability under acidic conditions.
  • Y 1 is preferably a divalent hydrocarbon group having 1 to 30 carbon atoms, more preferably a divalent saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably a linear alkanediyl group having 1 to 30 carbon atoms, and even more preferably an alkylene group having 1 to 30 carbon atoms.
  • the number of carbon atoms in Y 1 is preferably 2 to 16, more preferably 4 to 14, and even more preferably 6 to 12.
  • n1 is preferably 1.
  • R 1 is preferably a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.
  • R 1 is more preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, even more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 1 is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 5.
  • R 1 may be a substituted or unsubstituted monovalent aliphatic unsaturated hydrocarbon group having 2 to 30 carbon atoms.
  • R 1 is preferably an unsubstituted monovalent aliphatic unsaturated hydrocarbon group having 2 to 30 carbon atoms, more preferably a linear alkenyl group having 2 to 30 carbon atoms, even more preferably a linear alkenyl group having 2 to 10 carbon atoms, still more preferably a vinyl group, a 2-propenyl group, a 2-butenyl group or a 3-butenyl group, and particularly preferably a 2-propenyl group.
  • R 2 is preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably a hydrogen atom or an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a hydrogen atom or a linear alkyl group having 1 to 30 carbon atoms.
  • R 2 is a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms
  • the number of carbon atoms of R 2 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1.
  • R 3 , R 4 , R 5 and R 6 are each preferably independently a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a straight-chain alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 3 , R 4 , R 5 and R 6 is each independently preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1.
  • R 7 is preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 7 is preferably 5 to 27, more preferably 7 to 23, and even more preferably 9 to 21.
  • R 8 is preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 8 is preferably 5 to 27, more preferably 7 to 23, and even more preferably 9 to 21.
  • At least one of X1 and R1 in the general formula (1) is a group containing a vinyl group.
  • the composition of the present embodiment it is preferable that only one of X1 and R1 in the general formula (1) is a group containing a vinyl group.
  • the polymer obtained by polymerizing the monomer component containing the compound represented by the general formula (1) has an appropriate degree of crosslinking, and when the composition is used as a component of a coating composition, the coating composition has excellent film-forming properties.
  • the compound represented by general formula (1) can be produced, for example, by condensing 2,2,6,6-tetramethylpiperidin-4-ol with a carboxylic acid such as (meth)acrylic acid or a fatty acid to produce an ester compound, and then reacting this ester compound with an epoxy compound such as an alkyl glycidyl ether or an allyl glycidyl ether in the presence of a catalyst such as zinc chloride.
  • a carboxylic acid such as (meth)acrylic acid or a fatty acid
  • an epoxy compound such as an alkyl glycidyl ether or an allyl glycidyl ether in the presence of a catalyst such as zinc chloride.
  • the compound represented by general formula (1) is a compound represented by the following general formula (11).
  • Z 11 represents a single bond or an oxygen atom
  • R 12 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms
  • R 13 , R 14 , R 15 , R 16 , and R 18 each independently represent a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.
  • Z 11 represents a single bond
  • Z 11 does not have an atom, and the two atoms connected to Z 11 in general formula (11) are directly bonded.
  • Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms represented by R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 18 in general formula (11) include the same as the examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 in general formula (1).
  • Z11 in general formula (11) is preferably an oxygen atom.
  • the hydrophilicity of the compound represented by general formula (11) is further improved, and the composition of the present embodiment can form a dispersion having excellent stability under acidic conditions.
  • R 11 is preferably a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.
  • R 11 is more preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, even more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 11 is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 5.
  • R 12 is preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably a hydrogen atom or an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a hydrogen atom or a linear alkyl group having 1 to 30 carbon atoms.
  • R 12 is a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms
  • the number of carbon atoms of R 12 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1.
  • R 13 , R 14 , R 15 and R 16 are each preferably independently a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 13 , R 14 , R 15 and R 16 is each independently preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1.
  • R 18 is preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 18 is preferably 5 to 27, more preferably 7 to 23, and even more preferably 9 to 21.
  • the compound represented by general formula (11) can be produced, for example, by reacting an ester of 2,2,6,6-tetramethylpiperidin-4-ol and (meth)acrylic acid with an epoxy compound such as alkyl glycidyl ether in the presence of a catalyst such as zinc chloride.
  • the compound represented by general formula (1) may be a compound represented by the following general formula (21):
  • n2 represents 1 or 2.
  • Y 21 represents a single bond or a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms.
  • Z 21 represents a single bond or an oxygen atom.
  • R 23 , R 24 , R 25 , R 26 , and R 27 each independently represent a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.
  • Z 21 represents a single bond
  • Y 21 represents a single bond means that Y 21 does not have an atom, and the two carbon atoms connected to Y 21 are directly bonded.
  • ** represents a site bonded to an oxygen atom
  • R 22 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.
  • Examples of the substituted or unsubstituted monovalent hydrocarbon groups having 1 to 30 carbon atoms represented by R 22 , R 23 , R 24 , R 25 , R 26 and R 27 in general formula (21) and general formula (22) include the same as the examples of the substituted or unsubstituted monovalent hydrocarbon groups having 1 to 30 carbon atoms represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 in general formula (1).
  • Examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms represented by X21 in general formula (21) include the same as the examples of the substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms represented by R1 , R2 , R3 , R4 , R5 , R6 , R7 , and R8 in general formula (1).
  • examples of the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by X21 in general formula (21) include the same as those exemplified as the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by X1 in general formula (1).
  • examples of the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by Y 21 in general formula (21) include the same as the examples of the substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms represented by X 1 in general formula (1).
  • Z21 in general formula (21) is preferably an oxygen atom.
  • the hydrophilicity of the compound represented by general formula (21) is further improved, and the composition of the present embodiment can form a dispersion having excellent stability under acidic conditions.
  • Y 21 is preferably a divalent hydrocarbon group having 1 to 30 carbon atoms, more preferably a divalent saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably a linear alkanediyl group having 1 to 30 carbon atoms, and even more preferably an alkylene group having 1 to 30 carbon atoms.
  • the number of carbon atoms in Y 21 is preferably 2 to 16, more preferably 4 to 14, and even more preferably 6 to 12.
  • n2 is preferably 1.
  • R 22 is preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably a hydrogen atom or an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a hydrogen atom or a linear alkyl group having 1 to 30 carbon atoms.
  • R 22 is a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms
  • the number of carbon atoms of R 22 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1.
  • R 23 , R 24 , R 25 and R 26 are each preferably independently a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 23 , R 24 , R 25 and R 26 is each independently preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1.
  • R 27 is preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • the number of carbon atoms in R 27 is preferably 5 to 27, more preferably 7 to 23, and even more preferably 9 to 21.
  • the compound represented by general formula (21) can be produced, for example, by reacting an ester of 2,2,6,6-tetramethylpiperidin-4-ol with a monovalent or divalent carboxylic acid with an epoxy compound such as allyl glycidyl ether in the presence of a catalyst such as zinc chloride.
  • the content of the compound represented by general formula (1) relative to the total monomer components forming the polymer is not particularly limited, and can be, for example, 0.01 to 100% by mass. From the viewpoint of obtaining a composition capable of forming a dispersion with even better stability under acidic conditions, and from the viewpoint of obtaining a composition capable of imparting even better light resistance to a coating film obtained by applying the coating composition when used as a component of a coating composition, the content of the compound represented by general formula (1) relative to the total monomer components is preferably 0.1 to 50% by mass.
  • the content of the compound represented by general formula (1) relative to the total monomer components can be 0.01 to 10 mass%, preferably 0.1 mass% or more and less than 10 mass%, more preferably 0.3 to 5 mass%, and even more preferably 0.5 to 3 mass%.
  • the composition of this embodiment is particularly suitable as a vehicle for paints.
  • the content of the compound represented by general formula (1) relative to the total monomer components can be 10 to 100% by mass, preferably greater than 10% by mass and equal to or less than 100% by mass, more preferably 20 to 80% by mass, and even more preferably 30 to 50% by mass.
  • the composition of this embodiment is particularly suitable as a light stabilizer for paints.
  • Examples of monomer components that form a polymer and are not represented by the general formula (1) above include (meth)acrylic acid esters, (meth)acrylic acid, ethylene, propylene, 1-butene, butadiene, chloroethylene, styrene-based monomers, acrylonitrile, vinyl acetate, reactive emulsifiers having a double bond in the molecule, silane coupling agents having a double bond in the molecule, and ultraviolet absorbers having a double bond in the molecule. These may be used alone or in combination of two or more.
  • the monomer component that forms the polymer contains a reactive emulsifier.
  • the composition can form a dispersion that has even better stability under acidic conditions.
  • Reactive emulsifiers are, for example, those described in JP-B-49-46291, JP-A-58-203960, JP-A-61-222530, JP-A-62-100502, JP-A-62-104802, JP-A-62-11534, JP-A-63-23725, JP-A-63-91130, JP-A-63-319035, JP-A-04-256429, JP-A-04-50202, JP-A-04-502 04, JP-A-06-239908, JP-A-08-041113, JP-A-09-031113, JP-A-10-120712, JP-A-2002-265505, JP-A-2002-275115, JP-A-2002-301353, JP-A-2003-128709, JP-A-2020-117668, etc., and the technical contents of these are appropriately incorporated and made a part of this specification.
  • the content of the reactive emulsifier relative to the total monomer components can be, for example, 0.1 to 20% by mass.
  • the content of the reactive emulsifier relative to the total monomer components is preferably 0.5 to 15% by mass, more preferably 1 to 10% by mass, and even more preferably 2 to 5% by mass.
  • the monomer component that forms the polymer contains a (meth)acrylic acid ester.
  • the composition can form a dispersion that has even better stability under acidic conditions.
  • the (meth)acrylic acid ester may be used alone or in combination of two or more.
  • the composition of the present embodiment is used as a component of a paint composition, from the viewpoint of providing excellent film-forming properties to the paint composition, it is preferable that an acrylic acid ester and a methacrylic acid ester are used in combination as the (meth)acrylic acid ester.
  • examples of (meth)acrylic acid esters include methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, butyl methacrylate, isobutyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, cyclohexyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, etc.
  • More preferred is a combination of at least one selected from the group consisting of methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, butyl methacrylate, isobutyl methacrylate, hexyl methacrylate, and 2-ethylhexyl methacrylate, even more preferred is a combination of at least one selected from the group consisting of butyl acrylate, isobutyl acrylate, hexyl acrylate, and 2-ethylhexyl acrylate, and at least one selected from the group consisting of methyl methacrylate and ethyl methacrylate, and even more preferred is a combination of at least one selected from the group consisting of butyl acrylate, hexyl acrylate, and 2-ethylhexyl acrylate, and methyl methacrylate.
  • the monomer component that forms the polymer preferably contains a styrene-based monomer.
  • the composition can form a dispersion that has even better stability under acidic conditions.
  • styrene-based monomers examples include styrene, ⁇ -alkylstyrenes such as ⁇ -methylstyrene, alkylstyrenes such as vinyltoluene, and halostyrenes such as chlorostyrene.
  • the monomer components that form the polymer contain both a (meth)acrylic acid ester and a styrene-based monomer.
  • the composition can form a dispersion that has even better stability under acidic conditions.
  • the content of the (meth)acrylic acid ester relative to the total monomer components can be, for example, 0.1 to 99.9% by mass.
  • the content of the (meth)acrylic acid ester relative to the total monomer components is preferably 20 to 99% by mass, more preferably 40 to 98% by mass, even more preferably 80 to 97% by mass, and even more preferably 90 to 96% by mass.
  • the monomer component that forms the polymer preferably contains a monomer having an acidic functional group.
  • the composition when used as a component of a paint composition, the adhesion between the coating film obtained by applying the paint composition and the substrate to be painted is excellent. Also, in this case, when the composition is used as a component of a paint composition that contains a colorant such as a pigment, the dispersion stability of the colorant in the paint composition is excellent.
  • Examples of monomers having an acidic functional group include (meth)acrylic acid, maleic acid, fumaric acid, and styrene sulfonic acid. These may be used alone or in combination of two or more. Among these, (meth)acrylic acid is preferred, and acrylic acid is more preferred, from the viewpoint of improving the adhesion between the coating film obtained by applying the coating composition and the substrate to be coated when the composition is used as a component of a coating composition.
  • the content of the monomer having an acidic functional group relative to the total monomer components can be, for example, 0.01 to 20 mass%.
  • the content of the monomer having an acidic functional group relative to the total monomer components is preferably 0.05 to 10 mass%, more preferably 0.1 to 8 mass%, even more preferably 0.5 to 5 mass%, and even more preferably 1 to 3 mass%.
  • the weight average molecular weight of the polymer is not particularly limited, and may be, for example, 2,000 to 5,000,000.
  • the "weight average molecular weight” refers to the weight average molecular weight in terms of standard polystyrene measured by gel permeation chromatography (GPC).
  • the polymer may have a single layer structure or a multilayer structure such as a core-shell structure.
  • the volume average particle diameter of the polymer is not particularly limited and may be, for example, 50 to 1000 nm.
  • the "volume average particle diameter" refers to the volume average particle diameter measured by particle size distribution measurement using dynamic light scattering.
  • the composition of the present embodiment includes an aqueous dispersion medium.
  • the aqueous dispersion medium includes water or a mixture of water and a water-soluble organic solvent.
  • the water-soluble organic solvent is an organic solvent that is miscible with water, and examples thereof include acetone, methyl ethyl ketone, ethylene glycol, propylene glycol, methyl alcohol, ethyl alcohol, and isopropyl alcohol. These may be used alone or in combination of two or more.
  • the aqueous dispersion medium included in the composition of the present embodiment is preferably water.
  • composition of this embodiment preferably further contains an emulsifier other than the reactive emulsifier described above.
  • the composition can form a dispersion with even better stability under acidic conditions.
  • emulsifiers other than reactive emulsifiers include anionic surfactants such as fatty acid metal salts and alkylsulfonic acid metal salts, nonionic surfactants such as polyoxyalkylene alkyl ethers, cationic surfactants such as alkyltrimethylammonium salts, and amphoteric surfactants such as carboxybetaine surfactants.
  • the content thereof can be, for example, 0.01 to 20 parts by mass relative to 100 parts by mass of the polymer, and from the viewpoint of obtaining a composition capable of forming a dispersion with even better stability under acidic conditions, the content is preferably 0.1 to 15 parts by mass relative to 100 parts by mass of the polymer, more preferably 1 to 10 parts by mass, and even more preferably 2 to 5 parts by mass.
  • the nonvolatile content of the composition of this embodiment can be, for example, 10 to 80% by mass, and from the viewpoints of productivity and handleability, is preferably 20 to 70% by mass, and more preferably 30 to 60% by mass.
  • the nonvolatile content (mass %) of the composition can be calculated by weighing 1 g of the composition, drying it in a hot air dryer at a temperature of 110°C for 1 hour, measuring the mass (g) of the resulting residue, and multiplying this by 100.
  • the polymer is dispersed in an aqueous dispersion medium.
  • the composition of this embodiment can be used even more preferably as a component of a coating composition.
  • the method for producing the composition of the present embodiment includes a dispersing step of dispersing a polymer obtained by polymerizing a monomer component containing the compound represented by the above general formula (1) in an aqueous dispersion medium.
  • the method for producing a composition according to this embodiment makes it possible to produce a composition that can form a dispersion with excellent stability under acidic conditions.
  • the dispersion step preferably includes a step of emulsion polymerizing a monomer component containing a compound represented by general formula (1) in an aqueous dispersion medium.
  • the particle size of the polymer can be easily controlled by the polymerization conditions, and a polymer with a narrow particle size distribution can be obtained.
  • the method for producing the composition of this embodiment may include a step of polymerizing a monomer component containing a compound represented by general formula (1) by a radical polymerization method other than emulsion polymerization.
  • a production method include a method in which a monomer component containing a compound represented by general formula (1) is radically polymerized in an organic solvent such as xylene, the organic solvent is removed to isolate the polymer, and the obtained polymer is dispersed in an aqueous dispersion medium.
  • the polymerization initiator used to polymerize the monomer component containing the compound represented by general formula (1) is not particularly limited, and any known radical polymerization initiator can be used.
  • examples of such polymerization initiators include persulfates such as ferrous sulfate, ammonium persulfate, potassium persulfate, and sodium persulfate, bisulfites such as potassium bisulfite and sodium bisulfite, sulfites such as potassium sulfite and sodium sulfite, peroxides such as benzoyl peroxide, lauryl peroxide, methyl ethyl ketone peroxide, dicumyl peroxide, t-butyl hydroperoxide, hydrogen peroxide, cumene hydroperoxide, tert-butylperoxy-2-ethylhexanoate, and t-butylperoxyisobutyrate, and azo compounds such as azobisisobut
  • the amount of the polymerization initiator used is not particularly limited, and can be, for example, 0.01 to 20 parts by mass relative to a total of 100 parts by mass of the monomer components including the compound represented by general formula (1). From the viewpoint of improving the controllability of the polymerization reaction, it is preferably 0.05 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and even more preferably 0.5 to 2.5 parts by mass.
  • the polymerization of the monomer component containing the compound represented by general formula (1) may be carried out in the presence of a chain transfer agent.
  • the degree of crosslinking of the polymer can be reduced, and when the composition is used as a component of a coating composition, the coating composition has excellent film-forming properties.
  • chain transfer agents examples include mercaptan compounds such as n-dodecyl mercaptan, tert-dodecyl mercaptan, n-octyl mercaptan, n-tetradecyl mercaptan, n-hexyl mercaptan, and n-butyl mercaptan, halogen compounds such as carbon tetrachloride and ethylene bromide, disulfide compounds such as diphenyl disulfide, and ⁇ -methylstyrene dimer. These may be used alone or in combination of two or more.
  • the amount of the chain transfer agent used is not particularly limited, and may be, for example, 0.01 to 10 parts by mass per 100 parts by mass of the total of the monomer components containing the compound represented by general formula (1).
  • the coating composition of the present embodiment contains a polymer obtained by polymerizing a monomer component containing the compound represented by the above general formula (1).
  • the coating composition of this embodiment can form a dispersion that has excellent stability under acidic conditions.
  • the coating film obtained by applying the coating composition of this embodiment has excellent light resistance.
  • the coating composition of this embodiment may contain an aqueous dispersion medium.
  • the coating composition of this embodiment may contain the above-mentioned composition.
  • the content of the polymer obtained by polymerizing the monomer component containing the compound represented by the above general formula (1) in the coating composition of this embodiment is not particularly limited, and can be, for example, 0.01 to 100 mass %.
  • the paint composition may further contain pigments, plasticizers, film-forming agents, preservatives, anti-mold agents, defoamers, thickeners (viscosity adjusters), leveling agents, dispersants, anti-settling agents, heat resistance improvers, anti-skinning agents, slip agents, drying agents, anti-sagging agents, matting agents, light stabilizers, antioxidants, UV absorbers, etc., as necessary.
  • the coating composition of this embodiment can be suitably used for painting, for example, automobile exterior parts such as bumpers, radiator grilles, front grilles, front panels, fenders, pillars, pillar covers, door mirror stay covers, glass run channels, door mirror housings, lamp housings, wheel covers, spoilers, air spoilers, weather strips, window moldings, belt moldings, sunroofs, front end modules, door modules, back door modules, and exterior panels; building parts such as roofs, walls, floors, and window frames; and housings of home appliances such as refrigerators, washing machines, and vacuum cleaners.
  • automobile exterior parts such as bumpers, radiator grilles, front grilles, front panels, fenders, pillars, pillar covers, door mirror stay covers, glass run channels, door mirror housings, lamp housings, wheel covers, spoilers, air spoilers, weather strips, window moldings, belt moldings, sunroofs, front end modules, door modules, back door modules, and exterior panels
  • building parts such as roofs, walls, floors, and window frames
  • the article of the present embodiment is provided with a coating film obtained by applying the above-mentioned coating composition.
  • the article of this embodiment has excellent light resistance.
  • the article of this embodiment may, for example, include a substrate, with the coating film laminated on the substrate.
  • the article of this embodiment may also include a substrate and one or more undercoat layers laminated on the substrate, with the coating film laminated on the undercoat layers.
  • the article of this embodiment may include one or more coat layers laminated on the coating film.
  • Examples of materials for the substrate of the above-mentioned articles include metals such as zinc-plated steel, zinc alloy-plated steel, stainless steel, tin-plated steel, galvalume steel, and aluminum alloys; synthetic resins such as acrylic resin, polycarbonate resin, polyester resin, polystyrene resin, ABS resin, AS resin, vinyl chloride resin, polyamide resin, polyarylate resin, acrylic imide resin, and polyallyl diglycol carbonate resin; glass, ceramics, concrete, wood, and siding boards.
  • metals such as zinc-plated steel, zinc alloy-plated steel, stainless steel, tin-plated steel, galvalume steel, and aluminum alloys
  • synthetic resins such as acrylic resin, polycarbonate resin, polyester resin, polystyrene resin, ABS resin, AS resin, vinyl chloride resin, polyamide resin, polyarylate resin, acrylic imide resin, and polyallyl diglycol carbonate resin
  • glass, ceramics, concrete, wood, and siding boards examples of materials for the substrate of the above-mentioned articles.
  • the coating film can be formed, for example, by a method including a step of applying the coating composition onto a substrate or an undercoat layer.
  • Methods for applying the coating composition include known methods such as brush coating, bar coating, spray coating, dip coating, spin coating, and curtain coating.
  • the thickness of the coating is not particularly limited, but may be, for example, 10 to 300 ⁇ m.
  • articles of this embodiment include bumpers, radiator grilles, front grilles, front panels, fenders, pillars, pillar covers, door mirror stay covers, glass run channels, door mirror housings, lamp housings, wheel covers, spoilers, air spoilers, weather strips, window moldings, belt moldings, sunroofs, front end modules, door modules, back door modules, exterior panels and other automotive exterior parts, roofs, walls, floors, window frames and other architectural parts, and housings for home appliances such as refrigerators, washing machines, vacuum cleaners, etc.
  • the light stabilizer monomer component of the present embodiment is intended to be used in a composition containing a light stabilizer polymer obtained by polymerizing the light stabilizer monomer component and an aqueous dispersion medium.
  • the light stabilizer monomer component of the present embodiment contains a compound represented by the above general formula (1).
  • a composition can be obtained that can form a dispersion with excellent stability under acidic conditions.
  • the light stabilizer polymer of the present embodiment is intended to be used in a composition containing the light stabilizer polymer and an aqueous dispersion medium.
  • the light stabilizer polymer of the present embodiment is obtained by polymerizing a light stabilizer monomer component containing a compound represented by the above general formula (1).
  • a composition can be obtained that can form a dispersion with excellent stability under acidic conditions.
  • FIG. 1 A polymer obtained by polymerizing a monomer component containing a compound represented by the following general formula (1);
  • R 2 is a hydrogen atom or a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrogen atom or an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a hydrogen atom or a linear alkyl group having 1 to 30 carbon atoms.
  • R 2 has 1 to 10 carbon atoms, preferably 1 to 5, more preferably 1 to 2, and even more preferably 1.
  • n1 is 2.
  • composition according to [8], wherein Y 1 is a divalent hydrocarbon group having 1 to 30 carbon atoms, preferably a divalent saturated hydrocarbon group having 1 to 30 carbon atoms, more preferably a linear alkanediyl group having 1 to 30 carbon atoms, and even more preferably an alkylene group having 1 to 30 carbon atoms.
  • Y 1 has 2 to 16 carbon atoms, preferably 4 to 14 carbon atoms, and more preferably 6 to 12 carbon atoms.
  • R 1 is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a straight-chain alkyl group having 1 to 30 carbon atoms.
  • R 1 has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.
  • R 1 is a substituted or unsubstituted monovalent aliphatic unsaturated hydrocarbon group having 2 to 30 carbon atoms, preferably an unsubstituted monovalent aliphatic unsaturated hydrocarbon group having 2 to 30 carbon atoms, more preferably a linear alkenyl group having 2 to 30 carbon atoms, even more preferably a linear alkenyl group having 2 to 10 carbon atoms, still more preferably a vinyl group, a 2-propenyl group, a 2-butenyl group or a 3-butenyl group, and particularly preferably a 2-propenyl group.
  • R 3 , R 4 , R 5 and R 6 each independently have 1 to 10 carbon atoms, preferably 1 to 5, more preferably 1 to 2, and even more preferably 1.
  • the compound represented by the general formula (1) is any one of the above compounds No. 1 to No. 28.
  • R 11 is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, even more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a straight-chain alkyl group having 1 to 30 carbon atoms.
  • R 12 is a hydrogen atom or a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrogen atom or an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a hydrogen atom or a linear alkyl group having 1 to 30 carbon atoms.
  • R 13 , R 14 , R 15 and R 16 each independently represent a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, preferably a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, more preferably an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a linear alkyl group having 1 to 30 carbon atoms.
  • composition according to [24] wherein R 13 , R 14 , R 15 and R 16 each independently have 1 to 10 carbon atoms, preferably 1 to 5, more preferably 1 to 2, and even more preferably 1.
  • n2 represents 1 or 2
  • R 22 is a hydrogen atom or a substituted or unsubstituted monovalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, preferably a hydrogen atom or a substituted or unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrogen atom or an unsubstituted monovalent aliphatic saturated hydrocarbon group having 1 to 30 carbon atoms, and even more preferably a hydrogen atom or a straight-chain alkyl group having 1 to 30 carbon atoms.
  • Y 21 has 2 to 16 carbon atoms, preferably 4 to 14 carbon atoms, and more preferably 6 to 12 carbon atoms.
  • composition according to any one of [1] to [39], wherein the content of the compound represented by general formula (1) relative to all monomer components forming the polymer is 0.1 to 10 mass%, preferably 0.1 mass% or more and less than 10 mass%, more preferably 0.3 to 5 mass%, and even more preferably 0.5 to 3 mass%.
  • content of the compound represented by general formula (1) relative to all monomer components forming the polymer is 10 to 100 mass%, preferably more than 10 mass% and 100 mass% or less, more preferably 20 to 80 mass%, and even more preferably 30 to 50 mass%.
  • a monomer component for forming a polymer contains a reactive emulsifier.
  • the content of the reactive emulsifier relative to the total amount of the monomer components is 0.1 to 20 mass%, preferably 1 to 15 mass%, and more preferably 2 to 10 mass%.
  • a monomer component for forming a polymer contains a (meth)acrylic acid ester.
  • composition according to any one of [1] to [45] wherein a monomer component for forming a polymer contains a styrene-based monomer.
  • composition according to any one of [1] to [46], wherein a monomer component that forms a polymer contains a monomer having an acidic functional group.
  • a paint vehicle comprising the composition according to any one of [1] to [50].
  • a light stabilizer for coatings comprising the composition according to any one of [1] to [50].
  • a coating composition comprising a polymer obtained by polymerizing a monomer component containing the compound represented by the above general formula (1).
  • a coating composition comprising the composition according to any one of [1] to [50].
  • a coating film obtained by applying the coating composition according to any one of [53] to [55].
  • a method for producing a composition comprising a dispersing step of dispersing a polymer obtained by polymerizing a monomer component containing a compound represented by the following general formula (1) in an aqueous dispersion medium:
  • n1 represents 1 or 2
  • Y 1 represents a single bond or a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms
  • Z 1 represents a single bond or an oxygen atom
  • a compound represented by the following general formula (11): (In general formula (11), Z 11 represents a single bond or an oxygen atom, R 11 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms or a group represented by -C( O)-R 18 , R 12 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, and R 13 , R 14 , R 15 , R 16 , and R 18 each independently represent a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms.) [62] A compound represented by the following general formula (21): (In general formula (21), n2 represents 1 or 2, and when n2 is 1, X
  • the light stabilizer polymer according to [64] A light stabilizer polymer; An aqueous dispersion medium; A light stabilizer polymer for use in a composition comprising:
  • the present invention is not limited to the above-described embodiments.
  • the above-described embodiments are merely examples, and anything that has substantially the same configuration as the technical idea described in the claims of the present invention and exhibits similar effects is included within the technical scope of the present invention.
  • Synthesis Example 2 The same procedure as in Synthesis Example 1 was repeated except that 7.1 g of lauric acid chloride was used instead of methacrylic acid chloride and 4.0 g of allyl glycidyl ether was used instead of n-butyl glycidyl ether, to obtain 10.1 g of a pale yellow liquid.
  • Synthesis Example 3 The same procedure as in Synthesis Example 1 was repeated except that 10.0 g of stearic acid chloride was used instead of methacrylic acid chloride and 4.0 g of allyl glycidyl ether was used instead of n-butyl glycidyl ether, to obtain 11.9 g of a pale yellow liquid.
  • Example 1 First, 56.8 parts by mass of deionized water, 2.35 parts by mass of a reactive emulsifier (manufactured by ADEKA Corporation, trade name ADEKA REASOAP SR-10), 46.55 parts by mass of methyl methacrylate, 46.55 parts by mass of butyl acrylate, 1.9 parts by mass of acrylic acid, 0.95 parts by mass of compound No. 1, and 1.1 parts by mass of a 10% by mass aqueous solution of ammonium persulfate were uniformly mixed to prepare a dropping emulsion.
  • a reactive emulsifier manufactured by ADEKA Corporation, trade name ADEKA REASOAP SR-10
  • Example 2 First, 56.8 parts by mass of deionized water, 2.35 parts by mass of a reactive emulsifier (manufactured by ADEKA Corporation, product name ADEKA REASOAP SR-10), 33.25 parts by mass of methyl methacrylate, 28.5 parts by mass of styrene monomer, 31.35 parts by mass of 2-ethylhexyl acrylate, 1.9 parts by mass of acrylic acid, 0.95 parts by mass of Compound No. 1, and 1.1 parts by mass of a 10% by mass aqueous solution of ammonium persulfate were uniformly mixed to prepare an emulsion for dropping.
  • a reactive emulsifier manufactured by ADEKA Corporation, product name ADEKA REASOAP SR-10
  • 33.25 parts by mass of methyl methacrylate 28.5 parts by mass of styrene monomer
  • 31.35 parts by mass of 2-ethylhexyl acrylate 1.9 parts by mass of acrylic acid
  • Example 3 A composition was obtained in the same manner as in Example 2, except that Compound No. 13 was used in place of Compound No. 1.
  • Example 4 A composition was obtained in the same manner as in Example 2, except that compound No. 15 was used in place of compound No. 1.
  • compositions of Examples 1, 2, 3, 4, and Comparative Examples 1 and 2 were allowed to stand for 2 hours in an environment of 25° C. and then visually observed. As a result, the compositions of Examples 1, 2, 3, and 4 maintained a state in which the homogeneous polymer was uniformly dispersed in water, whereas the compositions of Comparative Examples 1 and 2 were aggregated and solidified.
  • compositions of Examples 1, 2, 3, 4, Comparative Example 1, and 2 are under acidic conditions because they contain acrylic acid as a raw material monomer. Under these conditions, it was found that the compositions of Examples 1, 2, 3, and 4 can form dispersions with excellent stability. On the other hand, it cannot be said that the compositions of Comparative Example 1 and Comparative Example 2 can form dispersions with sufficient stability.
  • composition of the present invention can form a dispersion with excellent stability.
  • Example 5 A composition is obtained in the same manner as in Example 2, except that compound No. 14 is used in place of compound No. 1.
  • Example 6 A composition is obtained in the same manner as in Example 2, except that a mixture of Compound No. 14 and Compound No. 15 (mass ratio 1:1) is used instead of Compound No. 1.
  • Example 7 A composition is obtained in the same manner as in Example 1, except that compound No. 13 is used in place of compound No. 1.
  • Example 8) A composition is obtained in the same manner as in Example 1, except that compound No. 14 is used in place of compound No. 1.
  • Example 9 A composition is obtained in the same manner as in Example 1, except that compound No. 15 is used in place of compound No. 1.
  • Example 10 A composition is obtained in the same manner as in Example 2, except that a mixture of Compound No. 14 and Compound No. 15 (mass ratio 1:1) is used instead of Compound No. 1.
  • Example 11 A composition is obtained in the same manner as in Example 1, except that acrylic acid is not used.
  • Example 12 A composition is obtained in the same manner as in Example 2, except that acrylic acid is not used.
  • Example 13 A composition is obtained in the same manner as in Example 3, except that acrylic acid is not used.
  • Example 14 A composition was obtained in the same manner as in Example 4, except that no acrylic acid was used.
  • Example 15 A composition is obtained in the same manner as in Example 5, except that acrylic acid is not used.
  • Example 16 A composition is obtained in the same manner as in Example 6, except that acrylic acid is not used.
  • Example 17 A composition is obtained in the same manner as in Example 7, except that acrylic acid is not used.
  • Example 18 A composition is obtained in the same manner as in Example 8, except that acrylic acid is not used.
  • Example 19 A composition is obtained in the same manner as in Example 9, except that no acrylic acid is used.
  • Example 20 A composition is obtained in the same manner as in Example 10, except that acrylic acid is not used.
  • Example 21 First, 30.40 parts by weight of deionized water, 14.00 parts by weight of reactive emulsifier (manufactured by ADEKA Corporation, trade name ADEKA REASOAP SR-10), 15.20 parts by weight of methyl methacrylate, 15.20 parts by weight of butyl acrylate, 1.35 parts by weight of acrylic acid, 30.40 parts by weight of compound No. 1 and 6.0 parts by weight of 10% by weight aqueous solution of ammonium persulfate are uniformly mixed to prepare a dropping emulsion.
  • reactive emulsifier manufactured by ADEKA Corporation, trade name ADEKA REASOAP SR-10
  • 15.20 parts by weight of methyl methacrylate 15.20 parts by weight of butyl acrylate
  • 1.35 parts by weight of acrylic acid 30.40 parts by weight of compound No. 1 and 6.0 parts by weight of 10% by weight aqueous solution of ammonium persulfate are uniformly mixed to prepare a dropping emulsion.
  • Example 22 A composition is obtained in the same manner as in Example 21, except that compound No. 13 is used in place of compound No. 1.
  • Example 23 A composition is obtained in the same manner as in Example 21, except that compound No. 14 is used in place of compound No. 1.
  • Example 24 A composition is obtained in the same manner as in Example 21, except that compound No. 15 is used in place of compound No. 1.
  • Example 25 A composition is obtained in the same manner as in Example 21, except that a mixture of Compound No. 14 and Compound No. 15 (mass ratio 1:1) is used instead of Compound No. 1.
  • Example 26 A composition is obtained in the same manner as in Example 21, except that acrylic acid is not used.
  • Example 27 A composition is obtained in the same manner as in Example 22, except that acrylic acid is not used.
  • Example 28 A composition is obtained in the same manner as in Example 23, except that acrylic acid is not used.
  • Example 29 A composition is obtained in the same manner as in Example 24, except that acrylic acid is not used.
  • Example 30 A composition is obtained in the same manner as in Example 25, except that acrylic acid is not used.

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Citations (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4946291B1 (https=) 1970-11-21 1974-12-09
JPS58203960A (ja) 1982-05-21 1983-11-28 Kao Corp 新規なスルホコハク酸ジエステル塩およびその製造法並びにこれを含有する反応性界面活性剤組成物
JPS61222530A (ja) 1985-03-28 1986-10-03 Sanyo Chem Ind Ltd 反応性乳化剤
JPS6211534A (ja) 1985-07-09 1987-01-20 Nippon Niyuukazai Kk 乳化重合用乳化剤
JPS62100502A (ja) 1985-10-28 1987-05-11 Dai Ichi Kogyo Seiyaku Co Ltd 乳化重合用乳化剤
JPS62104802A (ja) 1985-07-24 1987-05-15 Asahi Denka Kogyo Kk 乳化重合用乳化剤
JPS6323725A (ja) 1986-03-18 1988-02-01 Dai Ichi Kogyo Seiyaku Co Ltd 界面活性剤
JPS6391130A (ja) 1986-10-06 1988-04-21 Nippon Shokubai Kagaku Kogyo Co Ltd 反応性界面活性剤
JPS63319035A (ja) 1987-06-23 1988-12-27 Dai Ichi Kogyo Seiyaku Co Ltd 乳化重合用乳化剤
JPH03157460A (ja) * 1989-10-11 1991-07-05 Nippon Shokubai Kagaku Kogyo Co Ltd 硬化型塗料用組成物
JPH0450202A (ja) 1990-06-19 1992-02-19 Shin Etsu Chem Co Ltd 重合体スケール付着防止用溶液および重合体スケールの付着防止方法
JPH0450204A (ja) 1990-06-19 1992-02-19 Dai Ichi Kogyo Seiyaku Co Ltd 乳化重合用乳化剤
JPH04256429A (ja) 1990-12-27 1992-09-11 Arakawa Chem Ind Co Ltd 反応性乳化剤およびその製造法
JPH06239908A (ja) 1993-02-12 1994-08-30 Nippon Oil & Fats Co Ltd 反応性乳化剤
JPH07286119A (ja) * 1994-04-18 1995-10-31 Sofuto Kiyuukiyuu Corp:Kk 光劣化からの自動車塗膜保護組成物
JPH0841113A (ja) 1994-07-28 1996-02-13 Asahi Denka Kogyo Kk 新規反応性界面活性剤、乳化重合用乳化剤及び樹脂改質剤
JPH0931113A (ja) 1995-07-25 1997-02-04 Asahi Denka Kogyo Kk 界面活性剤、乳化重合用乳化剤、懸濁重合用分散剤及び樹脂改質剤
JPH10120712A (ja) 1996-10-14 1998-05-12 Asahi Denka Kogyo Kk 共重合体型界面活性剤
JP2002265505A (ja) 2001-03-08 2002-09-18 Asahi Denka Kogyo Kk 反応性界面活性剤
JP2002275115A (ja) 2001-03-19 2002-09-25 Asahi Denka Kogyo Kk 界面活性剤
JP2002301353A (ja) 2000-12-28 2002-10-15 Asahi Denka Kogyo Kk 界面活性剤
JP2003128709A (ja) 2001-10-18 2003-05-08 Asahi Denka Kogyo Kk 乳化重合用乳化剤又は懸濁重合用分散剤
JP2007009025A (ja) * 2005-06-29 2007-01-18 Nippon Shokubai Co Ltd 紫外線吸収能を有するエマルション
WO2008056678A1 (fr) * 2006-11-10 2008-05-15 Nippon Shokubai Co., Ltd. Composition de polymère absorbant le rayonnement ultraviolet dispersé dans l'eau
JP2013053207A (ja) * 2011-09-02 2013-03-21 Dainichiseika Color & Chem Mfg Co Ltd 耐光性塗料
JP2014123750A (ja) * 2014-01-17 2014-07-03 Asahi Kasei E-Materials Corp 太陽電池用コーティング組成物
JP2020117668A (ja) 2019-01-28 2020-08-06 株式会社日本触媒 新規エマルション
WO2023080221A1 (ja) * 2021-11-05 2023-05-11 株式会社Adeka 化合物、重合体、光安定剤組成物、樹脂組成物、塗料組成物、物品、シーリング材、成形品、耐候性樹脂組成物の製造方法および合成樹脂の耐候性向上方法

Patent Citations (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4946291B1 (https=) 1970-11-21 1974-12-09
JPS58203960A (ja) 1982-05-21 1983-11-28 Kao Corp 新規なスルホコハク酸ジエステル塩およびその製造法並びにこれを含有する反応性界面活性剤組成物
JPS61222530A (ja) 1985-03-28 1986-10-03 Sanyo Chem Ind Ltd 反応性乳化剤
JPS6211534A (ja) 1985-07-09 1987-01-20 Nippon Niyuukazai Kk 乳化重合用乳化剤
JPS62104802A (ja) 1985-07-24 1987-05-15 Asahi Denka Kogyo Kk 乳化重合用乳化剤
JPS62100502A (ja) 1985-10-28 1987-05-11 Dai Ichi Kogyo Seiyaku Co Ltd 乳化重合用乳化剤
JPS6323725A (ja) 1986-03-18 1988-02-01 Dai Ichi Kogyo Seiyaku Co Ltd 界面活性剤
JPS6391130A (ja) 1986-10-06 1988-04-21 Nippon Shokubai Kagaku Kogyo Co Ltd 反応性界面活性剤
JPS63319035A (ja) 1987-06-23 1988-12-27 Dai Ichi Kogyo Seiyaku Co Ltd 乳化重合用乳化剤
JPH03157460A (ja) * 1989-10-11 1991-07-05 Nippon Shokubai Kagaku Kogyo Co Ltd 硬化型塗料用組成物
JPH0450202A (ja) 1990-06-19 1992-02-19 Shin Etsu Chem Co Ltd 重合体スケール付着防止用溶液および重合体スケールの付着防止方法
JPH0450204A (ja) 1990-06-19 1992-02-19 Dai Ichi Kogyo Seiyaku Co Ltd 乳化重合用乳化剤
JPH04256429A (ja) 1990-12-27 1992-09-11 Arakawa Chem Ind Co Ltd 反応性乳化剤およびその製造法
JPH06239908A (ja) 1993-02-12 1994-08-30 Nippon Oil & Fats Co Ltd 反応性乳化剤
JPH07286119A (ja) * 1994-04-18 1995-10-31 Sofuto Kiyuukiyuu Corp:Kk 光劣化からの自動車塗膜保護組成物
JPH0841113A (ja) 1994-07-28 1996-02-13 Asahi Denka Kogyo Kk 新規反応性界面活性剤、乳化重合用乳化剤及び樹脂改質剤
JPH0931113A (ja) 1995-07-25 1997-02-04 Asahi Denka Kogyo Kk 界面活性剤、乳化重合用乳化剤、懸濁重合用分散剤及び樹脂改質剤
JPH10120712A (ja) 1996-10-14 1998-05-12 Asahi Denka Kogyo Kk 共重合体型界面活性剤
JP2002301353A (ja) 2000-12-28 2002-10-15 Asahi Denka Kogyo Kk 界面活性剤
JP2002265505A (ja) 2001-03-08 2002-09-18 Asahi Denka Kogyo Kk 反応性界面活性剤
JP2002275115A (ja) 2001-03-19 2002-09-25 Asahi Denka Kogyo Kk 界面活性剤
JP2003128709A (ja) 2001-10-18 2003-05-08 Asahi Denka Kogyo Kk 乳化重合用乳化剤又は懸濁重合用分散剤
JP2007009025A (ja) * 2005-06-29 2007-01-18 Nippon Shokubai Co Ltd 紫外線吸収能を有するエマルション
WO2008056678A1 (fr) * 2006-11-10 2008-05-15 Nippon Shokubai Co., Ltd. Composition de polymère absorbant le rayonnement ultraviolet dispersé dans l'eau
JP2013053207A (ja) * 2011-09-02 2013-03-21 Dainichiseika Color & Chem Mfg Co Ltd 耐光性塗料
JP2014123750A (ja) * 2014-01-17 2014-07-03 Asahi Kasei E-Materials Corp 太陽電池用コーティング組成物
JP2020117668A (ja) 2019-01-28 2020-08-06 株式会社日本触媒 新規エマルション
WO2023080221A1 (ja) * 2021-11-05 2023-05-11 株式会社Adeka 化合物、重合体、光安定剤組成物、樹脂組成物、塗料組成物、物品、シーリング材、成形品、耐候性樹脂組成物の製造方法および合成樹脂の耐候性向上方法

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