WO2024190887A1 - Kit de polymérisation dentaire - Google Patents

Kit de polymérisation dentaire Download PDF

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Publication number
WO2024190887A1
WO2024190887A1 PCT/JP2024/010105 JP2024010105W WO2024190887A1 WO 2024190887 A1 WO2024190887 A1 WO 2024190887A1 JP 2024010105 W JP2024010105 W JP 2024010105W WO 2024190887 A1 WO2024190887 A1 WO 2024190887A1
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agent
group
mass
compound
examples
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Japanese (ja)
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勇介 山田
宜久 紙本
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Sun Medical Co Ltd
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Sun Medical Co Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A61K6/62—Photochemical radical initiators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/76—Fillers comprising silicon-containing compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/77—Glass

Definitions

  • the present invention relates to a dental polymerization kit.
  • the component A contains a (meth)acrylate, an organic peroxide, and a filler.
  • the component B contains a (meth)acrylate, a thiourea derivative, a copper compound, a saccharin compound, a filler, and a photopolymerization initiator (see, for example, Patent Document 1).
  • the present invention provides a dental polymerization kit that can improve storage stability and adhesion to tooth structure while suppressing a decrease in color stability.
  • the present invention [1] includes a dental polymerization kit comprising an A component containing an acidic monomer having an acidic group and an ethylenically unsaturated group, an organic peroxide, and a specific imide compound represented by any one of the following general formulas (1) to (5), and an B component containing a tertiary amine.
  • R represents a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • R 21 represents a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • R 22 represents an alkylene group, an alkenylene group, or an arylene group.
  • R 31 represents a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • Each of R 32 and R 33 represents an aliphatic group or an aromatic group.
  • the present invention [2] includes the dental polymerization kit according to the above [1], wherein at least one of the agent A and the agent B contains a non-acidic monomer having no acidic group and an ethylenically unsaturated group.
  • the present invention [3] includes the dental polymerization kit of the above [2], in which the ratio of the specific imide compound to the total amount of the acidic monomer in the agent A and the non-acidic monomer in the agent A is 0.1 parts by mass or more per 100 parts by mass.
  • the present invention [4] includes the dental polymerization kit of the above [2] or [3], in which the ratio of the organic peroxide to 100 parts by mass of the total amount of the acidic monomer in the agent A and the non-acidic monomer in the agent A is 0.01 parts by mass or more.
  • the present invention [5] includes any one of the dental polymerization kits [1] to [4] above, in which both agent A and agent B are in the form of a paste.
  • the present invention [6] includes any one of the dental polymerization kits [1] to [5] above, in which both agent A and agent B contain a filler.
  • the present invention [7] includes any one of the dental polymerization kits [1] to [6] above, in which the agent B further contains a transition metal compound.
  • the present invention [8] includes the dental polymerization kit of the above [7], in which the transition metal compound contains a transition metal belonging to the fourth period of the periodic table.
  • the present invention includes the dental polymerization kit of the above [7], in which the transition metal compound is at least one of a copper compound, an iron compound, a cobalt compound, a chromium compound, a zinc compound, a manganese compound, and a vanadium compound.
  • the transition metal compound is at least one of a copper compound, an iron compound, a cobalt compound, a chromium compound, a zinc compound, a manganese compound, and a vanadium compound.
  • the present invention [10] includes any one of the dental polymerization kits [7] to [9] above, in which the transition metal compound is solid in the agent B, and when the agent A and the agent B are mixed, at least a portion of the transition metal compound is soluble in the acidic monomer in the agent A.
  • the present invention [11] includes the dental polymerization kit of the above [10], in which the transition metal compound is at least one of a copper compound, an iron compound, and a vanadium compound.
  • the present invention [12] includes any one of the dental polymerization kits [1] to [11] above, in which the agent A contains an inorganic peroxide.
  • the present invention includes any one of the dental polymerization kits [1] to [12] above, in which the agent A contains a photopolymerization initiator.
  • the present invention [14] includes any one of the dental polymerization kits [1] to [13] above, in which the agent B contains a reducing agent.
  • the dental polymerization kit of the present invention can improve storage stability and adhesion to tooth structure while preventing a decrease in color stability.
  • Two-component self-adhesive resin cement which is an example of a dental polymerization kit, is used in dental treatment, for example, to bond a prosthesis to a missing tooth site.
  • the two-component self-adhesive resin cement comprises component A and component B.
  • the two-component self-adhesive resin cement is used, for example, by mixing components A and B immediately before use and applying the resulting mixture.
  • the two-component self-adhesive resin cement is also used, for example, by applying component A and then component B.
  • “Self-adhesive” means that the pretreatment agent has sufficient adhesion to the tooth structure even without being applied to the tooth structure.
  • Agent A contains an acidic monomer, an organic peroxide, and a specific imide compound. Agent A contains a non-acidic monomer, a filler, an inorganic peroxide, and a photopolymerization initiator as necessary. In addition, when agent B does not contain a non-acidic monomer and a filler, agent A necessarily contains a non-acidic monomer and a filler. Agent A does not contain a tertiary amine and a reducing agent. In this embodiment, agent A is in a liquid or paste form.
  • the acidic monomer has an acidic group and an ethylenically unsaturated group.
  • acidic groups include carboxy groups, phosphate groups, thiophosphate groups, and sulfo groups.
  • the acidic monomer may contain only one type of acidic group, or may contain two or more types of acidic groups.
  • ethylenically unsaturated groups examples include acryloyl groups, methacryloyl groups, and vinyl groups.
  • acidic monomers having a carboxy group examples include aromatic carboxylic acid derivatives, aliphatic carboxylic acid derivatives, and amino acid derivatives.
  • aromatic carboxylic acid derivatives examples include benzoic acid derivatives, salicylic acid derivatives, phthalic acid derivatives, trimellitic acid derivatives, pyromellitic acid derivatives, naphthalene tricarboxylic acid derivatives, benzophenone tetracarboxylic acid derivatives, and biphenyl tetracarboxylic acid derivatives.
  • benzoic acid derivatives include 4-vinylbenzoic acid, 2-(meth)acryloyloxybenzoic acid, 3-(meth)acryloyloxybenzoic acid, 4-(meth)acryloyloxybenzoic acid, N-(meth)acryloyl-4-aminobenzoic acid, and N-(meth)acryloyl-5-aminobenzoic acid.
  • salicylic acid derivatives include 4-(meth)acryloylaminosalicylic acid and 5-(meth)acryloylaminosalicylic acid.
  • phthalic acid derivatives include 4-[(2-hydroxy-3-(meth)acryloyloxypropyl)amino]phthalic acid, 3-[N-methyl-N-(2-hydroxy-3-(meth)acryloyloxypropyl)amino]phthalic acid, and 4-[N-methyl-N-(2-hydroxy-3-(meth)acryloyloxypropyl)amino]phthalic acid.
  • trimellitic acid derivatives include 4-(meth)acryloyloxyalkyl trimellitic acid, 4-[2-hydroxy-3-(meth)acryloyloxy]butyl trimellitic acid, 2,3-bis(3,4-dicarboxybenzoyloxy)propyl(meth)acrylate, and 2-(3,4-dicarboxybenzoyloxy)-1,3-di(meth)acryloyloxypropane.
  • 4-(meth)acryloyloxyalkyl trimellitic acid include 4-(meth)acryloyloxymethyl trimellitic acid, 4-(meth)acryloyloxyethyl trimellitic acid, and 4-(meth)acryloyloxybutyl trimellitic acid.
  • pyromellitic acid derivatives include 1,4-di(meth)acryloyloxyethyl pyromellitic acid and the reaction product of 2-hydroxyethyl(meth)acrylate and pyromellitic acid dianhydride.
  • naphthalene tricarboxylic acid derivative is 6-(meth)acryloyloxyethylnaphthalene-1,2,6-tricarboxylic acid.
  • benzophenonetetracarboxylic acid derivative is the reaction product of 2-hydroxyethyl (meth)acrylate and 3,3',4,4'-benzophenonetetracarboxylic dianhydride.
  • biphenyltetracarboxylic acid derivative is the reaction product of 2-hydroxyethyl (meth)acrylate and 3,3',4,4'-biphenyltetracarboxylic dianhydride.
  • aliphatic carboxylic acid derivatives include maleic acid, a reaction product of 2-hydroxyethyl (meth)acrylate and maleic anhydride, and 11-(meth)acryloyloxy-1,1-undecanedicarboxylic acid.
  • amino acid derivatives include N,O-di(meth)acryloyloxytyrosine, O-(meth)acryloyloxytyrosine, N-(meth)acryloyloxytyrosine, N-(meth)acryloyloxyphenylalanine, a reaction product of N-phenylglycine with glycidyl (meth)acrylate, and a reaction product of N-tolylglycine with glycidyl (meth)acrylate.
  • the acidic monomer having a carboxy group is preferably an aromatic carboxylic acid derivative, more preferably a trimellitic acid derivative, more preferably 4-(meth)acryloyloxyalkyl trimellitic acid, more preferably 4-(meth)acryloyloxyethyl trimellitic acid, more preferably 4-methacryloyloxyethyl trimellitic acid.
  • acidic monomers having a phosphate group examples include aliphatic phosphate esters and aromatic phosphate esters.
  • aliphatic phosphate esters examples include (meth)acryloyloxyalkyl acid phosphate and bis[(meth)acryloyloxyalkyl] acid phosphate.
  • Examples of (meth)acryloyloxyalkyl acid phosphates include 2-(meth)acryloyloxyethyl acid phosphate, 2-(meth)acryloyloxypropyl acid phosphate, 3-(meth)acryloyloxypropyl acid phosphate, 4-(meth)acryloyloxybutyl acid phosphate, 6-(meth)acryloyloxyhexyl acid phosphate, 8-(meth)acryloyloxyoctyl acid phosphate, 10-(meth)acryloyloxydecyl acid phosphate, and 12-(meth)acryloyloxydodecyl acid phosphate.
  • bis[(meth)acryloyloxyalkyl] acid phosphates include bis[2-(meth)acryloyloxyethyl] acid phosphate, bis[2-(meth)acryloyloxypropyl] acid phosphate, and bis[3-(meth)acryloyloxypropyl] acid phosphate.
  • aromatic phosphate esters examples include 2-(meth)acryloyloxyethyl phenyl acid phosphate and 2-(meth)acryloyloxyethyl-p-methoxyphenyl acid phosphate.
  • the acidic monomer having a phosphoric acid group is preferably an aliphatic phosphoric acid ester, more preferably (meth)acryloyloxyalkyl acid phosphate, more preferably 10-(meth)acryloyloxydecyl acid phosphate, more preferably 10-methacryloyloxydecyl acid phosphate (MDP).
  • MDP 10-methacryloyloxydecyl acid phosphate
  • acidic monomers having a thiophosphate group examples include compounds in which the phosphate group of the acidic monomers having a phosphate group described above is replaced with a thiophosphate group.
  • a preferred example of the acidic monomer is an acidic monomer having a phosphate group.
  • Acidic monomers can be used alone or in combination of two or more types.
  • the proportion of acidic monomers in agent A is, for example, 0.1% by mass or more, preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and for example, 50% by mass or less, preferably 30% by mass or less, more preferably 20% by mass or less.
  • the ratio of the acidic monomer to the total amount of the non-acidic monomers in agent A and agent B is, for example, 1 part by mass or more, preferably 2 parts by mass or more, more preferably 5 parts by mass or more, and for example, 50 parts by mass or less, preferably 30 parts by mass or less, more preferably 20 parts by mass or less.
  • organic peroxides examples include diacyl peroxides, peroxy esters, dialkyl peroxides, peroxy ketals, ketone peroxides, and hydroperoxides.
  • Diacyl peroxides include, for example, benzoyl peroxide, diacetyl peroxide, 2,4-dichlorobenzoyl peroxide, decanoyl peroxide, 3,3,5-trimethylhexanoyl peroxide, lauroyl peroxide, and m-toluoyl peroxide.
  • peroxyesters examples include t-butylperoxybenzoate, bis-t-butylperoxyisophthalate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butylperoxy-2-ethylhexanoate, and t-butylperoxyisopropyl carbonate.
  • dialkyl peroxides examples include dicumyl peroxide, di-t-butyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, and 2,5-dimethyl-2,5-di(t-butylperoxy)-3-hexane.
  • peroxyketals examples include 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, 2,2-bis(t-butylperoxy)butane, 2,2-bis(t-butylperoxy)octane, and 4,4-bis(t-butylperoxy)valeric acid-n-butyl ester.
  • ketone peroxide is methyl ethyl ketone peroxide.
  • hydroperoxides examples include cumene hydroperoxide, t-butyl hydroperoxide, t-amyl hydroperoxide, p-diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, and p-methane hydroperoxide.
  • organic peroxide preferably, peroxyester is used, and more preferably, t-butyl peroxybenzoate (BPB) is used.
  • peroxyester preferably, peroxyester is used, and more preferably, t-butyl peroxybenzoate (BPB) is used.
  • BPB t-butyl peroxybenzoate
  • Organic peroxides can be used alone or in combination of two or more types.
  • the proportion of organic peroxide in agent A is, for example, 0.05% by mass or more, preferably 0.1% by mass or more, and for example, 1% by mass or less, preferably 0.5% by mass or less.
  • the ratio of the organic peroxide relative to 100 parts by mass of the total amount of the acidic monomer in agent A and the non-acidic monomer in agent A is, for example, 0.01 parts by mass or more, preferably 0.1 parts by mass or more, more preferably 0.3 parts by mass or more, and for example, 5 parts by mass or less, preferably 3 parts by mass or less, more preferably 1.5 parts by mass or less.
  • the ratio of organic peroxide to 100 parts by mass of the total of acidic monomers in agent A and non-acidic monomers in agent A is equal to or greater than the above lower limit, the self-adhesiveness can be improved.
  • the ratio of organic peroxide to 100 parts by mass of the total of acidic monomers in agent A and non-acidic monomers in agent A is equal to or less than the above upper limit, the deterioration of the storage stability of agent A can be suppressed.
  • General formula (1) represents saccharin, saccharin derivatives, and alkali metal salts thereof.
  • R represents a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • alkali metal atoms examples include lithium, potassium, and sodium.
  • Aliphatic groups include, for example, linear alkyl groups having 1 to 12 carbon atoms, or branched alkyl groups having 3 to 12 carbon atoms.
  • linear alkyl groups having 1 to 12 carbon atoms include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl groups.
  • Examples of branched alkyl groups having 3 to 12 carbon atoms include isopropyl, isobutyl, sec-butyl, tert-butyl, and 2-ethylhexyl groups.
  • aromatic groups include aromatic hydrocarbon groups and aromatic heterocyclic groups.
  • An example of an aromatic hydrocarbon group is a phenyl group.
  • aromatic heterocyclic groups include furyl, thienyl, pyrrolyl, and pyridyl groups.
  • Hydrogen atoms in the aliphatic and aromatic groups may be substituted with halogen atoms.
  • Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine.
  • Preferred examples of the specific imide compound represented by general formula (1) include saccharin, methylsaccharin (an example of a saccharin derivative), and sodium saccharin hydrate (an example of an alkali metal salt of saccharin).
  • General formula (2) shows a cyclic imide and an alkali metal salt thereof.
  • R1 shows a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • alkali metal atom include the above-mentioned alkali metal atoms.
  • aliphatic group include the above-mentioned aliphatic groups.
  • aromatic group include the above-mentioned aromatic groups.
  • R2 represents an alkylene group, an alkenylene group, or an arylene group.
  • alkylene groups examples include alkylene groups having 1 to 4 carbon atoms. Specific examples include methylene groups, ethylene groups, and propylene groups.
  • alkenylene groups include alkenylene groups having 1 to 4 carbon atoms. Specific examples include ethyleneylene groups.
  • An example of an arylene group is a phenylene group.
  • Hydrogen atoms in the alkylene group, alkenylene group, and arylene group may be substituted with the above-mentioned halogen atoms.
  • Preferred examples of the specific imide compound represented by general formula (2) include succinimide, glutarimide, and maleimide.
  • General formula (3) shows acyclic imides and their alkali metal salts.
  • R11 shows a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • alkali metal atom include the above-mentioned alkali metal atoms.
  • aliphatic group include the above-mentioned aliphatic groups.
  • aromatic group include the above-mentioned aromatic groups.
  • Each of R 12 and R 13 represents an aliphatic group or an aromatic group.
  • Examples of the aliphatic group include the aliphatic groups described above.
  • Examples of the aromatic group include the aromatic groups described above.
  • diacetamide is preferably used as a specific imide compound represented by general formula (3).
  • General formula (4) shows a cyclic sulfonimide and an alkali metal salt thereof.
  • R21 shows a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • the alkali metal atom include the above-mentioned alkali metal atom.
  • the aliphatic group include the above-mentioned aliphatic group.
  • the aromatic group include the above-mentioned aromatic group.
  • R22 represents an alkylene group, an alkenylene group, or an arylene group.
  • alkylene group include the alkylene group described above.
  • alkenylene group include the alkenylene group described above.
  • arylene group include the arylene group described above.
  • An example of a specific imide compound represented by general formula (4) is 4,4-difluoro-1,1,3,3-tetraoxide-1,3,2-dithiazetidine.
  • General formula (5) shows acyclic sulfonimide and its alkali metal salt.
  • R 31 shows a hydrogen atom, an alkali metal atom, an aliphatic group, or an aromatic group.
  • the alkali metal atom include the above-mentioned alkali metal atom.
  • the aliphatic group include the above-mentioned aliphatic group.
  • the aromatic group include the above-mentioned aromatic group.
  • Each of R 32 and R 33 represents an aliphatic group or an aromatic group.
  • Examples of the aliphatic group include the aliphatic groups described above.
  • Examples of the aromatic group include the aromatic groups described above.
  • Preferred examples of the specific imide compound represented by general formula (5) include dibenzenesulfonimide and N-phenylbis(trifluoromethanesulfonimide).
  • Specific imide compounds can be used alone or in combination of two or more types.
  • the ratio of the specific imide compound to the total amount of the acidic monomers in agent A and the non-acidic monomers in agent A, 100 parts by mass is, for example, 0.1 parts by mass or more, preferably 0.2 parts by mass or more, and more preferably 0.3 parts by mass or more, and is, for example, 10 parts by mass or less, preferably 6 parts by mass or less, and more preferably 3 parts by mass or less.
  • the ratio of the specific imide compound to 100 parts by mass of the total of the acidic monomers in agent A and the non-acidic monomers in agent A is equal to or greater than the above lower limit, polymerization of the non-acidic monomers on the tooth surface can be promoted, and adhesion to the tooth can be improved.
  • the ratio of the specific imide compound to 100 parts by mass of the total of the acidic monomers in agent A and the non-acidic monomers in agent A is equal to or less than the above upper limit, all of the specific imide compound can be dissolved in the non-acidic monomers in agent A.
  • the ratio of the specific imide compound to 100 parts by mass of the tertiary amine in agent B is, for example, 5 parts by mass or more, preferably 15 parts by mass or more, and, for example, 30 parts by mass or less, preferably 500 parts by mass or less, preferably 400 parts by mass or less, more preferably 300 parts by mass or less.
  • Tertiary amines will be explained later.
  • Non-acidic Monomer does not have the above-mentioned acidic group, but has the above-mentioned ethylenically unsaturated group.
  • Non-acidic monomers are classified into those that have a hydroxyl group, those that have a urethane bond, and those that do not have a hydroxyl group or a urethane bond.
  • non-acidic monomers having a hydroxyl group examples include mono(meth)acrylates and di(meth)acrylates.
  • Examples of mono(meth)acrylates having a hydroxyl group include 2-hydroxyethyl(meth)acrylate, 3-hydroxypropyl(meth)acrylate, 6-hydroxyhexyl(meth)acrylate, and dihydroxypropyl mono(meth)acrylate.
  • Examples of mono(meth)acrylates having a hydroxyl group include 2-hydroxyethyl(meth)acrylate, and more preferably 2-hydroxyethyl methacrylate (HEMA).
  • An example of a di(meth)acrylate having a hydroxyl group is a bisphenol A derivative.
  • An example of a bisphenol A derivative having a hydroxyl group is 2,2-bis[4-(3-(meth)acryloyloxy-2-hydroxypropoxy)phenyl]propane.
  • UDMA UDMA
  • Examples of mono(meth)acrylates that do not have a hydroxyl group or a urethane bond include alkyl(meth)acrylates.
  • Examples of alkyl(meth)acrylates include methyl(meth)acrylate, ethyl(meth)acrylate, and butyl(meth)acrylate.
  • di(meth)acrylates that do not have hydroxyl groups or urethane bonds include alkanediol di(meth)acrylates, polyalkylene glycol di(meth)acrylates, and bisphenol A derivatives.
  • alkanediol di(meth)acrylate examples include ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, and neopentyl glycol di(meth)acrylate.
  • a preferred example of the alkanediol di(meth)acrylate is neopentyl glycol dimethacrylate (NPGDMA).
  • polyalkylene glycol di(meth)acrylates examples include diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, and polypropylene glycol di(meth)acrylate.
  • a preferred example of the polyalkylene glycol di(meth)acrylate is triethylene glycol di(meth)acrylate (TEGDMA).
  • An example of a bisphenol A derivative that does not have a hydroxyl group or a urethane bond is ethoxylated bisphenol A dimethacrylate (EBPADMA).
  • Non-acidic monomers can be used alone or in combination of two or more types.
  • Agent A contains at least a non-acidic monomer having a hydroxyl group and a non-acidic monomer having a urethane bond among the non-acidic monomers described above.
  • the proportion of non-acidic monomers in agent A is, for example, 5% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, and for example, 95% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less.
  • filler examples include conventionally known fillers that can be used in dental materials.
  • examples of the filler include silica, silica alumina, alumina, alumina quartz, glass, titania, zirconia, and ytterbium fluoride.
  • examples of the silica include fumed silica.
  • examples of the glass include barium glass.
  • the filler may be surface-treated with a coupling agent or the like to be hydrophobic or hydrophilic.
  • Fillers can be used alone or in combination of two or more types.
  • the proportion of the filler in agent A is, for example, 0.5% by mass or more, preferably 5% by mass or more, more preferably 15% by mass or more, and for example, 97% by mass or less, preferably 95% by mass or less, more preferably 90% by mass or less, more preferably 85% by mass or less, more preferably 75% by mass or less.
  • inorganic peroxides examples include persulfuric acid compounds, perphosphate compounds, perchloric acid compounds, and hydrogen peroxide derivatives.
  • persulfate compounds include sodium persulfate, potassium persulfate, calcium persulfate, magnesium persulfate, and ammonium persulfate.
  • perphosphate compounds include sodium perphosphate, potassium perphosphate, calcium perphosphate, magnesium perphosphate, and ammonium perphosphate.
  • perchlorate compounds include sodium perchlorate, potassium perchlorate, calcium perchlorate, magnesium perchlorate, and ammonium perchlorate.
  • hydrogen peroxide derivatives include hydrogen peroxide and urea peroxide.
  • the inorganic peroxide is a persulfate compound, more preferably, sodium persulfate or potassium persulfate.
  • Inorganic peroxides can be used alone or in combination of two or more types.
  • the proportion of inorganic peroxide in agent A is, for example, 0.01 mass% or more, preferably 0.05 mass% or more, more preferably 0.1 mass% or more, and for example, 10 mass% or less, preferably 7 mass% or less, more preferably 5 mass% or less.
  • the ratio of inorganic peroxide relative to 100 parts by mass of the total amount of the acidic monomer in agent A and the non-acidic monomer in agent A or agent B is, for example, 0.5 parts by mass or more, preferably 1 part by mass or more, and for example, 15 parts by mass or less, preferably 10 parts by mass or less.
  • Photopolymerization Initiator The photopolymerization initiator generates radicals when exposed to light.
  • photopolymerization initiators include (bis)acylphosphine oxides, ⁇ -diketones, ketals, thioxanthone derivatives, coumarin and its derivatives, and anthraquinone and its derivatives.
  • Examples of (bis)acylphosphine oxides include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylmethoxyphenylphosphine oxide, 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide, and 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide.
  • Examples of ⁇ -diketones include camphorquinone.
  • Examples of ketals include benzyl dimethyl ketal and benzyl diethyl ketal.
  • Examples of thioxanthone derivatives include 2-chlorothioxanthone and 2,4-diethylthioxanthone.
  • Examples of coumarin and its derivatives include coumarin, 3,3'-carbonylbis(7-diethylaminocoumarin), 3-benzoyl-5,7-dimethoxycoumarin, 3-benzoyl-7-dimethylaminocoumarin, 3-carboxycoumarin, and 3-ethoxycarbonyl-6-methoxycoumarin.
  • anthraquinone and its derivatives examples include anthraquinone, 1-bromoanthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 1,2-benzanthraquinone, 1-methylanthraquinone, 2-ethylanthraquinone, and 1-hydroxyanthraquinone.
  • the photopolymerization initiator is preferably an ⁇ -diketone, more preferably camphorquinone (CQ).
  • Photopolymerization initiators can be used alone or in combination of two or more types.
  • the proportion of the photopolymerization initiator in agent A is, for example, 0.001% by mass or more, preferably 0.01% by mass or more, and for example, 1% by mass or less, preferably 0.1% by mass or less.
  • the ratio of the photopolymerization initiator relative to 100 parts by mass of the total amount of the acidic monomer in agent A and the non-acidic monomer in agent A or agent B is, for example, 0.01 parts by mass or more, preferably 0.05 parts by mass or more, and for example, 1 part by mass or less, preferably 0.5 parts by mass or less.
  • the agent A may contain a polymerization inhibitor, a thickener, a coupling agent, an ultraviolet absorber, a fluorescent agent, a pigment, and a solvent, as necessary.
  • a polymerization inhibitor is dibutylhydroxytoluene (BHT).
  • Agent B contains a tertiary amine.
  • Agent B contains a reducing agent, a transition metal compound, a non-acidic monomer, and a filler as necessary.
  • agent B necessarily contains a non-acidic monomer and a filler.
  • Agent B does not contain an acidic monomer, an organic peroxide, an inorganic peroxide, or a specific imide compound.
  • Agent B is in a liquid or paste form.
  • Tertiary Amines include, for example, aromatic tertiary amines.
  • aromatic tertiary amines examples include N,N-dialkyltoluidine, N,N-bis(hydroxyalkyl)toluidine, N,N-dialkylaniline, and dialkylaminobenzoic acid esters.
  • N,N-dialkyltoluidine examples include N,N-dimethyl-p-toluidine and N,N-diethyl-p-toluidine.
  • N,N-bis(hydroxyalkyl)toluidines examples include N,N-bis(2-hydroxyethyl)-p-toluidine (BHEPT) and N,N-bis(2-hydroxypropyl)-p-toluidine.
  • N,N-dialkylanilines examples include N,N-dimethylaniline and N,N-diethylaniline.
  • dialkylaminobenzoate esters examples include methyl 4-(dimethylamino)benzoate, ethyl 4-(dimethylamino)benzoate (EDAB), 2-butoxyethyl 4-(dimethylamino)benzoate, and isoamyl 4-(dimethylamino)benzoate.
  • Tertiary amines can be used alone or in combination of two or more types.
  • a combination of N,N-bis(hydroxyalkyl)toluidine and a dialkylaminobenzoic acid ester is preferable, and a combination of N,N-bis(2-hydroxyethyl)-p-toluidine and ethyl 4-(dimethylamino)benzoate is more preferable.
  • the proportion of tertiary amine in agent B is, for example, 0.1% by mass or more, preferably 0.5% by mass or more, and for example, 10% by mass or less, preferably 5% by mass or less.
  • the ratio of tertiary amine to 100 parts by mass of organic peroxide in agent A is, for example, 100 parts by mass or more, preferably 130 parts by mass or more, and for example, 200 parts by mass or less, preferably 170 parts by mass or less.
  • (2-2) Reducing Agent examples include aromatic amino acids, sulfinic acids or salts thereof, thiourea compounds, phosphorous compounds, and sulfurous compounds.
  • aromatic amino acids examples include N-phenylglycinic acid, sodium N-phenylglycinate, and potassium N-phenylglycinate.
  • Sulfinic acids and their salts include, for example, aromatic sulfinic acids and their salts.
  • Aromatic sulfinic acids include, for example, benzenesulfinic acid, o-toluenesulfinic acid, p-toluenesulfinic acid, ethylbenzenesulfinic acid, decylbenzenesulfinic acid, dodecylbenzenesulfinic acid, chlorobenzenesulfinic acid, fluorobenzenesulfinic acid, and naphthalenesulfinic acid.
  • salts of aromatic sulfinic acid include lithium benzenesulfinate, sodium benzenesulfinate, potassium benzenesulfinate, magnesium benzenesulfinate, calcium benzenesulfinate, strontium benzenesulfinate, barium benzenesulfinate, butylamine salt of benzenesulfinic acid, aniline salt of benzenesulfinic acid, toluidine salt of benzenesulfinic acid, phenylenediamine salt of benzenesulfinic acid, diethylamine salt of benzenesulfinic acid, diphenylamine salt of benzenesulfinic acid, triethylamine salt of benzenesulfinic acid, tributylamine salt of benzenesulfinic acid, ammonium salt of benzenesulfinic acid, tetramethylbenzenesulfinic acid, etc.
  • ethylammonium trimethylbenzylammonium benzenesulfinate, lithium o-toluenesulfinate, sodium o-toluenesulfinate, potassium o-toluenesulfinate, calcium o-toluenesulfinate, cyclohexylamine salt of o-toluenesulfinate, aniline salt of o-toluenesulfinate, ammonium salt of o-toluenesulfinate, tetraethylammonium o-toluenesulfinate, lithium p-toluenesulfinate, sodium p-toluenesulfinate (STS), potassium p-toluenesulfinate, calcium p-toluenesulfinate, barium p-toluenesulfinate, ethylamine salt of p-toluenes
  • thiourea compounds for example, thiourea, methylthiourea, ethylthiourea, n-propylthiourea, isopropylthiourea, cyclohexylthiourea, benzylthiourea, phenylthiourea, acetylthiourea, benzoylthiourea, adamantylthiourea, (2-pyridyl)thiourea, 1-(2-tetrahydrofurfuryl)-2-thiourea, N,N'-dimethylthiourea, N,N'-diethylthiourea, N,N'-di-n-propylthiourea, N,N'-di-i
  • TMTU trimethylthiourea
  • Examples of phosphorous compounds include inorganic phosphorous compounds and organic phosphorous compounds.
  • inorganic phosphite compounds include calcium hypophosphite and sodium phosphite.
  • organic phosphite compounds include diethyl phosphite, dibutyl phosphite, diisopropyl phosphite, di-n-propyl phosphite, triphenyl phosphite, triallyl phosphite, diethyl phosphite, dibutyl phosphite, diisopropyl phosphite, di-n-propyl phosphite, triphenyl phosphite, and triallyl phosphite.
  • sulfurous acid compounds examples include inorganic sulfurous acid compounds and organic sulfurous acid compounds.
  • inorganic sulfite compounds include lithium sulfite, sodium sulfite, potassium sulfite, calcium sulfite, and sodium hydrogen sulfite.
  • organic sulfurous acid compounds examples include diethyl sulfite, di-n-propyl sulfite, diisopropyl sulfite, glycol sulfite, 1,3-propylene sulfite, and diallyl sulfite.
  • thiosulfate compounds include sodium thiosulfate, calcium thiosulfate, potassium thiosulfate, and magnesium thiosulfate.
  • Reducing agents can be used alone or in combination of two or more types.
  • the reducing agent is preferably a combination of a sulfinic acid or its salt with a thiourea compound, more preferably a combination of an aromatic sulfinic acid or its salt with an alkylthiourea, more preferably a combination of p-toluenesulfinic acid or sodium p-toluenesulfinate with a trialkylthiourea, and more preferably a combination of sodium p-toluenesulfinate with trimethylthiourea.
  • the proportion of the reducing agent in agent B is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and for example, 30% by mass or less, preferably 20% by mass or less, more preferably 10% by mass or less.
  • the ratio of the reducing agent to 100 parts by mass of the inorganic peroxide in agent A is, for example, 10 parts by mass or more, preferably 20 parts by mass or more, for example, 100 parts by mass or less, preferably 50 parts by mass or less.
  • the transition metal compound contains a transition metal atom belonging to the fourth period of the periodic table.
  • the periodic table is the IUPAC Periodic Table of the Elements (version date 1 December 2018).
  • transition metal atoms include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), and gallium (Ga).
  • transition metal atoms include titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn), and more preferred examples of transition metal atoms include vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).
  • transition metal compounds include oxides, hydroxides, halides, carboxylates, sulfates, nitrates, carbonates, and complexes of transition metals.
  • halides include chlorides and bromides.
  • carboxylates include formates, acetates, oleates, acrylates, gluconates, phthalates, and citrates.
  • a transition metal complex has a transition metal atom as the central metal and ligands that coordinate to the transition metal atom.
  • Examples of the ligands include diketone-based ligands, amine-based ligands, thiol-based ligands, urea-based ligands, and thiourea-based ligands.
  • Examples of the diketone-based ligands include acetylacetonate.
  • Examples of the amine-based ligands include alkanediamines, benzimidazole, and benzothiazole.
  • Examples of the thiol-based ligands include mercaptoethanol, mercaptotriazole, mercaptobenzothiazole, and mercaptobenzimidazole.
  • Examples of the urea-based ligands include urea and ethyleneurea.
  • Examples of the thiourea-based ligands include thiourea, acetylthiourea, pyridylthiourea, and ethylenethiourea.
  • transition metal compounds include copper compounds, iron compounds, cobalt compounds, chromium compounds, zinc compounds, manganese compounds, and vanadium compounds.
  • copper compounds include copper(II) hydroxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(II) formate, copper(I) acetate, copper(II) acetate, copper(II) sulfate, copper(II) nitrate, copper(I) iodide, basic copper(II) carbonate, copper(I) oxide, copper(II) oxide, metallic copper, copper(II) oleate, copper(II) acrylate, copper(II) gluconate, copper(II) phthalate, copper(II) citrate, copper(II) acetylacetonate, mercaptobenzothiazole copper, 1,3-propanediamine copper, benzimidazole copper, benzothiazole copper, mercaptobenzimidazole copper (MBI-Cu), and copper thiourea.
  • iron compounds include iron(II) hydroxide, iron(III) oxide hydroxide, iron(II) chloride, iron(III) chloride, iron(I) bromide, iron(II) bromide, iron(II) acetate, iron(III) acetate, iron(II) carbonate, iron(II) oxide, iron(III) oxide, iron(II, III) oxide, metallic iron, iron(II) sulfate, iron(III) sulfate, iron(III) acetylacetonate, iron(III) citrate, and iron(II) gluconate.
  • cobalt compounds include cobalt(II) hydroxide, cobalt(II) chloride, cobalt(II) acetate, cobalt(II) bromide, basic cobalt carbonate, cobalt(II) sulfate, cobalt(II) oxide, cobalt(III) oxide, cobalt(II,III) oxide, metallic cobalt, cobalt(II) nitrate, and cobalt(III) acetylacetonate.
  • chromium compounds include chromium(III) acetate, chromium(II) chloride, chromium(III) chloride, chromium(IV) chloride, chromium(II) bromide, chromium(III) bromide, chromium(III) fluoride, chromium(V) fluoride, chromium(III) oxide, chromium(III) oxide, chromium(IV) oxide, chromium(VI) oxide, silver(I) chromate, chromium(III) nitrate, potassium dichromate, chromium(III) acetylacetonate, and chromium(III) hexafluoroacetylacetonate.
  • Examples of zinc compounds include zinc acetate, zinc chloride, zinc bromide, zinc iodide, zinc oxide, zinc sulfide, zinc nitrate, zinc sulfate, zinc phosphate, zinc diphosphate, zinc lactate, zinc salicylate, zinc stearate, zinc gluconate, zinc acrylate, and zinc 2-mercaptobenzothiazole.
  • manganese compounds include manganese(II) chloride, manganese(II) bromide, manganese(II) carbonate, manganese(II) fluoride, manganese(II) iodide, manganese(II) nitrate, manganese(IV) oxide, manganese(II) acetate, manganese(III) acetate, manganese(II) phosphate, manganese(II) sulfate, manganese(II) acetylacetonate, and manganese(III) acetylacetonate.
  • vanadium compounds include vanadium(III) chloride, vanadium(III) bromide, metallic vanadium, vanadium(II) oxide, vanadium(III) oxide, vanadium(V) oxide, vanadium(IV) oxyacetylacetonate, vanadium(III) acetylacetonate, oxovanadium(IV) oxalate, vanadium(IV) stearate oxide, vanadium(IV) oxide sulfate, ammonium vanadate(V), and sodium orthovanadate(V).
  • the transition metal compound is solid in agent B.
  • agent B contains the components in agent B and a water-insoluble transition metal compound powder that may be acquired by moisture absorption during storage.
  • the amount of the transition metal compound dissolved in 100 g of water at 20°C and 1 atm is, for example, 5 g or less, preferably 4 g or less, and more preferably 3 g or less.
  • the average particle size is, for example, 0.01 ⁇ m or more, preferably 0.1 ⁇ m or more, more preferably 1 ⁇ m or more, and, for example, 500 ⁇ m or less, preferably 100 ⁇ m or less, and more preferably 50 ⁇ m or less.
  • transition metal compound is a solid in component B, at least a portion of the transition metal compound is soluble in the acidic monomer in component A when components A and B are mixed.
  • the transition metal compound is preferably at least one of a copper compound, an iron compound, and a vanadium compound.
  • Transition metal compounds can be used alone or in combination of two or more types.
  • the proportion of the transition metal compound in agent B is, for example, 0.0001 mass% or more, preferably 0.0005 mass% or more, more preferably 0.001 mass% or more, and for example, 1 mass% or less, preferably 0.5 mass% or less, more preferably 0.3 mass% or less.
  • the ratio of the transition metal compound to 100 parts by mass of the reducing agent is, for example, 0.001 parts by mass or more, preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and is, for example, 10 parts by mass or less, preferably 5 parts by mass or less, more preferably 3 parts by mass or less.
  • the ratio of the transition metal compound to 100 parts by mass of the inorganic peroxide in Agent A is, for example, 0.001 parts by mass or more, preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and is, for example, 10 parts by mass or less, preferably 5 parts by mass or less, more preferably 3 parts by mass or less.
  • Non-acidic Monomers examples include the same monomers as the non-acidic monomers in the A component.
  • the proportion of non-acidic monomers in agent B is not limited.
  • the proportion of non-acidic monomers in agent B is, for example, 5% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, and for example, 99% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less.
  • the proportion of the filler in agent B is, for example, 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass, and for example, 97% by mass or less, preferably 95% by mass or less, more preferably 90% by mass or less.
  • Additives Agent B may contain a polymerization inhibitor, a neutralizing agent, a thickening agent, a solvent, a coupling agent, an ultraviolet absorbing agent, a fluorescent agent, and a pigment, if necessary.
  • the explanations of the polymerization inhibitor, the thickening agent, the solvent, the coupling agent, the ultraviolet absorbing agent, the fluorescent agent, and the pigment in agent B are the same as those of the polymerization inhibitor, the thickening agent, the solvent, the coupling agent, the ultraviolet absorbing agent, the fluorescent agent, and the pigment in agent A.
  • An example of a neutralizing agent is calcium hydroxide.
  • a mixture of components A and B is applied to at least one of the tooth structure and the prosthesis to bond the two together.
  • radicals are generated by an oxidation-reduction reaction between organic and inorganic peroxides and specific imide compounds, reducing agents, and tertiary amines.
  • transition metal compounds react with reducing agents, dissolved oxygen, and oxidizing agents (organic and inorganic peroxides) to generate radicals.
  • the generated radicals polymerize acidic and non-acidic monomers.
  • dental polymerization kits are used to polymerize acidic and non-acidic monomers in dental treatment.
  • the mixture of components A and B hardens as the acidic and non-acidic monomers polymerize, bonding the prosthesis to the tooth structure.
  • an acidic monomer, an organic peroxide, and a specific imide compound are mixed in the agent A, and a tertiary amine is mixed in the agent B.
  • the dental polymerization kit may be a two-part dental self-adhesive composite resin.
  • the two-part dental self-adhesive composite resin is used in dental treatment, for example, to fill missing teeth.
  • the dental polymerization kit may be a two-component dental coating agent.
  • the two-component dental coating agent is used in dental treatment, for example, to coat the surface of tooth tissue.
  • Agent A and Agent B According to the formulations in Tables 1 to 4, for each of Agent A and Agent B, first, the monomer liquid components were mixed to prepare a monomer liquid, and then a dispersing component (a component that disperses in a solid state in the monomer liquid) was added to the monomer liquid and mixed with a centrifugal mixer. In this way, Agent A and Agent B in a paste form were prepared.
  • a dispersing component a component that disperses in a solid state in the monomer liquid
  • Agent A or B gelled or hardened during or immediately after preparation.
  • the tensile adhesive strength is 2 MPa or more.
  • the tensile adhesion strength is less than 2 MPa.
  • the mixture of agent A and agent B stored at 65° C. for one week was cured by irradiating both sides with light for 10 seconds each using a PENCURE 2000 to obtain a 80 ⁇ m-thick cured product B.
  • the cured product B was immersed in water at 37° C. for about 24 hours and then dried, and the L * value, a * value, and b * value of the cured product B were measured against a white background.
  • the color difference ⁇ E between the cured products A and B was calculated from the L * , a * , and b * values of the cured product A and the L * , a * , and b * values of the cured product B, and evaluated according to the following criteria.
  • A: ⁇ E is 3.0 or less.
  • ⁇ E is greater than 3.0 and less than or equal to 4.5.
  • ⁇ E is greater than 4.5 and less than or equal to 6.0.
  • ⁇ E is greater than 6.0 and less than or equal to 9.0.
  • the dental polymerization kit of the present invention is used in dental treatment.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Biophysics (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention concerne un kit de polymérisation dentaire utilisé pour polymériser, dans un traitement dentaire, un monomère non acide n'ayant pas de groupe acide mais ayant un groupe éthyléniquement insaturé ; un monomère acide ayant un groupe acide et un groupe éthyléniquement insaturé, un peroxyde organique et un composé imide spécifique étant mélangés dans un agent A, et une amine tertiaire étant mélangée dans un agent B.
PCT/JP2024/010105 2023-03-16 2024-03-14 Kit de polymérisation dentaire Ceased WO2024190887A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3880662A (en) * 1973-01-08 1975-04-29 B D K Ltd Inc Porcelain mix for dental appliances
JP2003162061A (ja) * 2001-09-14 2003-06-06 Fuji Photo Film Co Ltd ポジ型レジスト組成物
JP2013252425A (ja) * 2012-05-16 2013-12-19 Heraeus Medical Gmbh ペースト様骨セメント
WO2022014492A1 (fr) * 2020-07-15 2022-01-20 三井化学株式会社 Initiateur de polymérisation, kit de préparation de composition durcissable, composition durcissable, produit durci et matériau dentaire
WO2022209944A1 (fr) * 2021-03-29 2022-10-06 サンメディカル株式会社 Kit de polymérisation dentaire

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3880662A (en) * 1973-01-08 1975-04-29 B D K Ltd Inc Porcelain mix for dental appliances
JP2003162061A (ja) * 2001-09-14 2003-06-06 Fuji Photo Film Co Ltd ポジ型レジスト組成物
JP2013252425A (ja) * 2012-05-16 2013-12-19 Heraeus Medical Gmbh ペースト様骨セメント
WO2022014492A1 (fr) * 2020-07-15 2022-01-20 三井化学株式会社 Initiateur de polymérisation, kit de préparation de composition durcissable, composition durcissable, produit durci et matériau dentaire
WO2022209944A1 (fr) * 2021-03-29 2022-10-06 サンメディカル株式会社 Kit de polymérisation dentaire

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