Classifications

• • 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
  • A61K6/61—Cationic, anionic or redox initiators
• • 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
  • A61K6/64—Thermal 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
  • A61K6/71—Fillers
• • 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
  • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
  • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
  • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2/00—Processes of polymerisation
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2/00—Processes of polymerisation
  • C08F2/46—Polymerisation initiated by wave energy or particle radiation
  • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
  • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents

Definitions

• the present disclosure relates to a polymerization accelerator, a polymerization initiator, a curable composition preparation kit, a curable composition, a cured product, and a dental material.
• cement is used as a tooth substitute for repairing large tooth defects.
• the scope of use of cement has expanded.
• a photopolymerization initiator, a chemical polymerization initiator, and the like may be used for polymerization of a curable composition for dental materials such as cement.
• a chemical polymerization initiator system is a redox type polymerization initiator that combines an oxidizing agent and a reducing agent.
• a redox type polymerization initiator for example, a polymerization initiator system using an organic peroxide as an oxidizing agent and an aromatic amine compound as a reducing agent is known.
• Patent Document 1 discloses a redox initiator system containing sulfite.
• Patent Document 1 International Publication No. 2017/100231
• Patent Document 1 the polymerization initiator described in Patent Document 1 has room for improvement in terms of monomer polymerizability.
• the problem to be solved by an embodiment of the present disclosure is a polymerization accelerator, a polymerization initiator, a curable composition preparation kit, a curable composition, a cured product, and a curable composition that can satisfactorily improve the polymerizability of monomers.
• Our goal is to provide dental materials.
• R B1 is an n-valent hydrocarbon group
• R B2 and R B3 are each independently a monovalent hydrocarbon group
• n is an integer of 1 or 2.
• a polymerization initiator comprising the phosphonite compound according to any one of ⁇ 1> to ⁇ 3>, an oxidizing agent, and a reducing agent.
• the oxidizing agent includes an organic peroxide
• the first agent includes the transition metal compound and the organic peroxide
• Any one of the monomer (1) in the first agent or the monomer (2) in the second agent includes an acidic group-containing monomer according to any one of ⁇ 5> to ⁇ 7>. Kit for preparing curable composition.
• the monomer (1) in the first agent includes an acidic group-containing monomer
• ⁇ 12> The total content of the phosphonite compound contained in the first part and the second part is 0.1% by mass to 1.5% by mass based on the total mass of the curable composition to be prepared.
• ⁇ 13> A curable composition comprising the phosphonite compound according to any one of ⁇ 1> to ⁇ 3>, an oxidizing agent, a reducing agent, and a monomer.
• ⁇ 14> A cured product of the curable composition according to ⁇ 13>.
• ⁇ 15> A dental material comprising the cured product according to ⁇ 14>.
• a polymerization accelerator, a polymerization initiator, a kit for preparing a curable composition, a curable composition, a cured product, and a dental material are provided that can satisfactorily improve the polymerizability of monomers. can do.
• a numerical range indicated using “ ⁇ ” means a range that includes the numerical values listed before and after " ⁇ " as the minimum and maximum values, respectively.
• the upper limit or lower limit described in a certain numerical range may be replaced with the upper limit or lower limit of another numerical range described step by step.
• the upper limit or lower limit described in a certain numerical range may be replaced with the value shown in the Examples.
• a combination of two or more preferred embodiments is a more preferred embodiment.
• the amount of each component means the total amount of the multiple types of substances, unless otherwise specified.
• (meth)acrylic means acrylic and methacryl
• (meth)acryloyl means acryloyl and methacryloyl.
• a or B means at least one of A and B, and may include both A and B (for example, a mixture of A and B).
• the polymerization accelerator of the present disclosure includes a phosphonite compound. By using a polymerization accelerator containing a phosphonite compound, the polymerizability of the monomer can be favorably improved.
• the polymerization accelerator of the present disclosure may contain one or more types of phosphonite compounds, or may contain two or more types of phosphonite compounds.
• the phosphonite compound may be any trivalent organic phosphorus compound in which a carbon atom is bonded to a phosphorus atom.
• the phosphonite compound contained in the polymerization accelerator of the present disclosure preferably includes a structure represented by the following general formula (X).
• * indicates the bonding position to the carbon atom.
• the three * marks are preferably bonding positions to a carbon atom contained in a hydrocarbon group, and more preferably bonding positions to a carbon atom contained in a benzene ring.
• the phosphonite compound may contain one structure represented by general formula (X), or may contain two or more structures.
• the phosphonite compound preferably contains two structures represented by the general formula (X), and the two structures represented by the general formula (X) are bonded via a divalent linking group (preferably a biphenyl structure). It is more preferable to include a skeleton containing
• the phosphonite compound contained in the polymerization accelerator of the present disclosure preferably contains a compound represented by the following general formula (Y).
• R B1 is an n-valent hydrocarbon group
• R B2 and R B3 are each independently a monovalent hydrocarbon group
• n is an integer of 1 or 2.
• n-valent hydrocarbon group in R B1 examples include an n-valent aliphatic hydrocarbon group, an n-valent alicyclic hydrocarbon group, an n-valent aromatic hydrocarbon group, a combination of two or more of these, etc. It will be done.
• the monovalent hydrocarbon group in R B1 is preferably an alkyl group, a phenyl group, a biphenyl group, or the like.
• the hydrogen atom of the phenyl group or biphenyl group in R B1 may be substituted with a substituent such as an alkyl group.
• the divalent hydrocarbon group in R B1 is preferably an alkylene group, a phenylene group, a 4,4'-biphenylene group, a 4,3'-biphenylene group, a biphenylene group such as a 3,3'-biphenylene group, or the like.
• the hydrogen atom contained in the phenylene group or biphenylene group in R B1 may be substituted with a substituent such as an alkyl group.
• R B2 and R B3 each independently represent a monovalent hydrocarbon group, preferably an alkyl group, a phenyl group, or the like.
• the hydrogen atom contained in the phenyl group in R B2 and R B3 may be substituted with an alkyl group such as a tert-butyl group or n-butyl group.
• n is an integer of 1 or 2, preferably 2.
• phosphonite compound contained in the polymerization accelerator of the present disclosure include, for example, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene-di-phosphonite, -tert-butyl-5-methylphenyl)4,4'-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butylphenyl)4,3'-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butylphenyl)4,3'-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butylphenyl)4,3'-biphenylene-di-phosphonite, -di-tert-
• the polymerization accelerator of the present disclosure may be a polymerization accelerator consisting only of a phosphonite compound, or may be a polymerization accelerator consisting of a phosphonite compound and another polymerization accelerator.
• Other polymerization accelerators include phosphite compounds, sulfite compounds, inorganic salts, thiourea, and the like. When using other polymerization accelerators, one type may be used alone, or two or more types may be used in combination.
• phosphite compounds include triphenyl phosphite, trisnonylphenyl phosphite, tricresyl phosphite, diphenyl mono(2-ethylhexyl) phosphite, diphenyl monodecyl phosphite, diphenyl mono(tridecyl) phosphite, tris Examples include (2,4-di-tert-butylphenyl) phosphite.
• sulfite compounds include ethylene sulfite, propylene sulfite, dimethyl sulfite, diethyl sulfite, ethyl methyl sulfite, methyl-n-propyl sulfite, ethyl-n-propyl sulfite, and di-n-propyl sulfite.
• examples include sulfite, diphenyl sulfite, methylphenyl sulfite, ethyl sulfite, dibenzyl sulfite, benzyl methyl sulfite, benzylethyl sulfite, and the like.
• inorganic salts include sodium sulfite, calcium sulfite, potassium sulfite, potassium nitrate, potassium chloride, potassium sulfate, and sodium chloride.
• thiourea examples include acetylthiourea, phenylthiourea, triethylthiourea, tetramethylthiourea, dimethylthiourea, diphenylthiourea, and the like.
• the content of the phosphonite compound may be 50% by mass to 99% by mass, and 60% by mass based on the total amount of the polymerization accelerator. It may be from 70% to 97% by weight, or from 70% to 97% by weight.
• the content of the other polymerization accelerator is 0.5% by mass to 30% by mass based on the total amount of the polymerization accelerator.
• the content may be 1% by mass to 20% by mass, or 1.5% by mass to 10% by mass.
• the polymerization initiator of the present disclosure includes the aforementioned phosphonite compound or the polymerization accelerator of the present disclosure, an oxidizing agent, and a reducing agent.
• the polymerization initiator of the present disclosure is a redox polymerization initiator that combines an oxidizing agent and a reducing agent.
• the content of the phosphonite compound or the content of the polymerization promoter is preferably 1 part by mass to 40 parts by mass, and 3 parts by mass to 30 parts by mass, based on 100 parts by mass of the polymerization initiator. It is more preferably 5 parts by mass to 20 parts by mass.
• the polymerization initiator of the present disclosure includes an oxidizing agent.
• the oxidizing agent is not particularly limited as long as it can be used as a redox polymerization initiator, and examples thereof include peroxides.
• peroxides examples include organic peroxides and inorganic peroxides, and the peroxide in the present disclosure preferably includes an organic peroxide.
• organic peroxide (organic peroxide)
• Typical organic peroxides include hydroperoxide, peroxyester, ketone peroxide, peroxyketal, dialkyl peroxide, diacyl peroxide, peroxydicarbonate, and the like.
• hydroperoxide is preferable because even if the curable composition is provided in a packaged form and stored for a long period of time, there is little variation in the operable time.
• One type of organic peroxide may be used alone, or a plurality of types may be used in combination.
• the hydroperoxides include cumene hydroperoxide, t-butyl hydroperoxide, t-hexyl hydroperoxide, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3, Examples include 3-tetramethylbutyl hydroperoxide and t-amyl hydroperoxide.
• any known peroxy ester may be used without any restriction as long as it contains an acyl group on one side of the peroxy group (-O-O- group) and a hydrocarbon group (or a similar group) on the other side. I can do it.
• Specific examples include ⁇ , ⁇ -bis(neodecanoylperoxy)diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl- 1-Methyl ethyl peroxy neodecanoate, t-hexyl peroxy neodecanoate, t-butyl peroxy neodecanoate, t-hexyl peroxy pivalate, t-butyl peroxy pivalate, 1,1 , 3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, 1-cyclohexyl-1-methylethylperoxy -2-ethylhexanoate, t-hexylperoxy 2-
• ketone peroxide examples include methyl ethyl ketone peroxide, cyclohexanoperoxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, and acetylacetone peroxide.
• Peroxyketals include 1,1-bis(t-hexylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-butyl peroxy) 3,3,5-trimethylcyclohexanone, 1,1-bis(t-butylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)cyclodecane, 2,2-bis(t-butylperoxy)cyclohexane, oxy)butane, n-butyl 4,4-bis(t-butylperoxy)valerate, 2,2-bis(4,4-di-t-butylperoxycyclohexyl)propane, and the like.
• dialkyl peroxides examples include ⁇ , ⁇ -bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, and t-butylcumylbenzene.
• dialkyl peroxides examples include luperoxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane-3, and the like.
• diacyl peroxide examples include isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearyl peroxide, and succinic acid peroxide. , m-toluoylbenzoyl peroxide, and benzoyl peroxides.
• peroxydicarbonate examples include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis(4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, di- Examples include 2-ethylhexyl peroxydicarbonate, di-2-methoxybutyl peroxydicarbonate, and di(3-methyl-3-methoxybutyl)peroxydicarbonate.
• inorganic peroxide examples include peroxodisulfate and peroxodiphosphate, and among these, peroxodisulfate is preferred from the viewpoint of curability.
• peroxodisulfate examples include sodium peroxodisulfate, potassium peroxodisulfate, aluminum peroxodisulfate, and ammonium peroxodisulfate.
• the above peroxodisulfates may be used alone or in combination of multiple types.
• sodium peroxodisulfate, potassium peroxodisulfate, and ammonium peroxodisulfate are preferred.
• the content of the oxidizing agent is preferably 20 parts by mass to 90 parts by mass, more preferably 30 parts by mass to 80 parts by mass, based on 100 parts by mass of the polymerization initiator.
• the amount is preferably 40 parts by mass to 70 parts by mass, and more preferably 40 parts by mass to 70 parts by mass.
• the polymerization initiator of the present disclosure includes a reducing agent.
• the reducing agent is not particularly limited as long as it can be used in redox polymerization initiators, and examples thereof include ascorbic acids, sulfinic acids, amine compounds, transition metal compounds, and the like.
• ascorbic acids examples include ascorbic acid, ascorbic acid derivatives, and salts thereof. From the viewpoint of improving the adhesiveness of the resulting cured product, it is preferable to use an ascorbic acid derivative or a salt thereof.
• salts of ascorbic acid include alkali metal salts of ascorbic acid, alkaline earth metal salts of ascorbic acid, and more specifically, sodium salts, potassium salts, magnesium salts, calcium salts, etc. of ascorbic acid. It will be done.
• ascorbic acid derivatives include compounds in which a part of the structure of the ascorbic acid skeleton has been substituted, and compounds in which substituents have been introduced, oxidized, reduced, atoms have been replaced, etc. to ascorbic acid.
• the ascorbic acid derivative may be a compound in which at least one of the four hydroxyl groups contained in ascorbic acid is substituted with another group.
• the ascorbic acid derivative preferably includes a structure in which at least one of the hydroxyl groups contained in ascorbic acid is substituted with an ether bond bonded to a carbon atom.
• salts of ascorbic acid derivatives include alkali metal salts of ascorbic acid derivatives, alkaline earth metal salts of ascorbic acid derivatives, and more specifically, sodium salts, potassium salts, magnesium salts, and calcium salts of ascorbic acid derivatives. Examples include salt. Among these, calcium salts are preferred from the viewpoint of balance between polymerizability and adhesiveness.
• the ascorbic acid derivative or its salt may contain a structure in which at least one of the four hydroxyl groups contained in ascorbic acid is replaced with an ether bond bonded to a carbon atom. It is preferable that ascorbic acid contains a structure in which two of the four hydroxyl groups contained in the ascorbic acid are substituted with ether bonds bonded to carbon atoms.
• the ascorbic acid derivative preferably includes a structure represented by the following general formula (A).
• * indicates the bonding position with the carbon atom.
• Two * in the general formula (A) may be bonded to the same carbon atom to form a 1,3-dioxolane skeleton.
• the ascorbic acid derivative preferably contains a compound represented by the following general formula (B).
• R 1B and R 2B are each independently a hydrogen atom or a monovalent organic group. At least one of R 1B and R 2B is preferably a monovalent organic group.
• the monovalent organic group in R 1B and R 2B is preferably an organic group having 1 to 12 carbon atoms, more preferably an organic group having 1 to 10 carbon atoms, and an organic group having 3 to 10 carbon atoms. It is more preferable that
• one of R 1B or R 2B may be a hydrogen atom, and the other of R 1B or R 2B may be a monovalent organic group having 1 to 10 carbon atoms.
• the monovalent organic group in R 1B and R 2B may be an organic group containing an oxygen atom, a nitrogen atom, a sulfur atom, etc., or a hydrocarbon group to which an oxygen atom, a nitrogen atom, a sulfur atom, etc. are bonded. It may also be a hydrocarbon group.
• the salt of the ascorbic acid derivative may be a salt of a compound represented by general formula (B), or may be an alkali metal salt or an alkaline earth metal salt of a compound represented by general formula (B). From the viewpoint of balance between polymerizability and adhesive properties, calcium salts of compounds represented by general formula (B) are preferred.
• R 1B and R 2B are preferably each independently a hydrogen atom or a monovalent organic group. Furthermore, one of R 1B or R 2B is a hydrogen atom, and the other of R 1B or R 2B is a monovalent organic group having 1 to 10 carbon atoms, or R 1B and R 2B are each independently It is preferably a monovalent organic group having 1 to 10 carbon atoms.
• R 1B or R 2B When one of R 1B or R 2B is a hydrogen atom, and the other of R 1B or R 2B is a monovalent organic group having 1 to 10 carbon atoms, the other of R 1B or R 2B is a monovalent organic group having 1 to 10 carbon atoms. It is preferably a monovalent organic group having 5 carbon atoms, more preferably a monovalent organic group having 1 to 3 carbon atoms, even more preferably a methyl group, ethyl group, propyl group or isopropyl group, and isopropyl group. A group is particularly preferred.
• R 1B and R 2B are each independently a monovalent organic group having 1 to 10 carbon atoms
• R 1B and R 2B are each independently a monovalent organic group having 1 to 5 carbon atoms. It is preferably a monovalent organic group having 1 to 3 carbon atoms, more preferably a methyl group, ethyl group, propyl group or isopropyl group, and particularly preferably a methyl group.
• ascorbic acid represented by the following general formula (C) and an aldehyde compound represented by the following general formula (D) or a ketone compound represented by the following general formula (E) are acetalized.
• An example of this method is to carry out a chemical reaction (see broken line).
• R in the above general formula (D) is the same as R 1B or R 2B in the above general formula (B).
• the two R's in the above general formula (E) are the same as R 1B and R 2B in the above general formula (B).
• the two R's in the above general formula (E) may be the same or different.
• Examples of the aldehyde compound represented by the above general formula (D) include butanal, isobutanal, hexanal, octanal, dodecanal, and the like.
• Examples of the ketone compound represented by the above general formula (E) include acetone, methyl ethyl ketone, and methyl isobutyl ketone. These compounds may be used alone or in combination of two or more.
• an ascorbic acid derivative represented by the following general formula (B) and an alkali metal salt represented by the following general formula (F) are combined.
• a reaction method alkali metalation reaction
• X represents an alkali metal
• R represents, for example, a carbonate group or a hydroxyl group.
• alkali metal salt represented by the above general formula (F) include sodium hydroxide, sodium hydrogen carbonate, sodium carbonate, calcium hydroxide, and calcium carbonate. These may be used alone or in combination of two or more.
• reaction conditions may be adjusted as appropriate.
• sulfinic acids examples include sulfinic acid compounds or salts thereof.
• sulfinic acid compound or its salt examples include alkanesulfinic acid or its salt, alicyclic sulfinic acid or its salt, and aromatic sulfinic acid or its salt.
• Salts of sulfinic acid compounds include lithium salts, sodium salts, potassium salts, rubidium salts, cesium salts, magnesium salts, calcium salts, strontium salts, iron salts, zinc salts, ammonium salts, tetramethylammonium salts, tetraethylammonium salts, etc. is exemplified.
• alkanesulfinic acid examples include methanesulfinic acid.
• alicyclic sulfinic acid examples include cyclohexane sulfinic acid and cyclooctane sulfinic acid.
• Aromatic sulfinic acids include benzenesulfinic acid, p-toluenesulfinic acid, o-toluenesulfinic acid, ethylbenzenesulfinic acid, decylbenzenesulfinic acid, dodecylbenzenesulfinic acid, 2,4,6-trimethylbenzenesulfinic acid, 2, Examples include 4,6-triisopropylbenzenesulfinic acid, chlorobenzenesulfinic acid, and naphthalenesulfinic acid.
• amine compound examples of the amine compound as a reducing agent include aromatic amine compounds, aliphatic amine compounds, and heterocyclic amine compounds. From the viewpoint of improving polymerizability, the amine compound preferably contains an aromatic amine compound. Aromatic amine compounds contain aromatic hydrocarbon groups in their structure. Further, the aromatic amine compound in the present disclosure does not include a heterocyclic aromatic compound.
• aromatic amine compounds include aromatic primary amine compounds such as aniline and toluidine; N-methylaniline, N-methyl-p-toluidine, N-phenylglycine (NPG), N-tolylglycine (NTG), N,N-(3-methacryloyloxy-2-hydroxypropyl)phenylglycine (NPG-GMA)
• Aromatic secondary amine compounds such as aromatic substituted amino acid compounds or salts thereof such as aromatic substituted glycine or its alkali metal salts, alkaline earth metal salts, amine salts, ammonium salts, etc.; N,N-dimethylaniline (DMA), N,N-dibenzylaniline, N,N-dimethyl-p-toluidine (DMPT), N,N-diethyl-p-toluidine, N,N-di(2-hydroxy ethyl)-p-toluidine (DEPT), N,N-dimethyl-p-ethylan
• an aliphatic amine compound containing at least one selected from the group consisting of primary, secondary and tertiary amino groups is preferable, and aliphatic amine compounds containing only tertiary amino groups are preferable.
• Compounds are more preferred.
• a heterocyclic amine compound containing at least one selected from the group consisting of primary, secondary, and tertiary amino groups is preferable, and heterocyclic amine compounds containing only tertiary amino groups are preferable. Cyclic amine compounds are more preferred.
• aliphatic amine compounds examples include EDTA (ethylenediaminetetraacetic acid), NTA (nitrilotetraacetic acid), DTPA (diethylenetriaminepentaacetic acid), HEDTA (hydroxyethylethylenediaminetriacetic acid), and TTHA (triethylenetetraminehexaacetic acid).
• EDTA ethylenediaminetetraacetic acid
• NTA nitrilotetraacetic acid
• DTPA diethylenetriaminepentaacetic acid
• HEDTA hydroxyethylethylenediaminetriacetic acid
• TTHA triethylenetetraminehexaacetic acid
• acetic acid PDTA series (1,3-propanediaminetetraacetic acid), DPTA-OH series (1,3-diamino-2-hydroxypropane tetraacetic acid), HIDA series (hydroxyethyliminodiacetic acid), DHEG series (dihydroxyethyl Glycine), GEDTA type (glycol ether diamine tetraacetic acid), CMGA type (dialboxymethylglutamic acid), EDDS type ((S,S)-ethylenediamine disuccinic acid) and EDTMP type (ethylenediaminetetra(methylenephosphonic acid)), N,N-dimethyl-N',N'-bis(2-dimethylaminoethyl)ethylenediamine (Me6TREN), N,N'-dimethyl-1,2-phenylenediamine, 2-(methylamino)phenol, 3-( methylamino)-2-butanol, N,N'-bis(1,1-dimethyl
• Heterocyclic amine compounds include, for example, heterocyclic amine compounds that can function as monodentate, bidentate, or tridentate heterocyclic electron donor ligands.
• the aliphatic amine compound or heterocyclic amine compound is preferably N,N-dimethyl-N',N'-bis(2-dimethylaminoethyl)ethylenediamine, 2,2'-bipyridine, N-butyl-2- Pyridylmethanimine, 4,4'-di-tert-butyl-2,2'-dipyridine, 4,4'-dimethyl-2,2'-dipyridine, 4,4'-dinonyl-2,2'-dipyridine, N-dodecyl-N-(2-pyridylmethylene)amine, 1,1,4,7,10,10-hexamethyl-triethylenetetramine, N-octadecyl-N-(2-pyridylmethylene)amine, N-octyl- 2-pyridylmethanimine, N,N,N',N",N"-pentamethyl-diethylenetriamine, 1,4,8,11-tetracycl
• transition metal compound examples include copper compounds, vanadium compounds, molybdenum compounds, scandium compounds, titanium compounds, chromium compounds, manganese compounds, iron compounds, cobalt compounds, and nickel compounds.
• the transition metal compound contains at least one of a copper compound and a vanadium compound, and more preferably a copper compound.
• Copper compounds include copper acetate, copper isobutyrate, copper gluconate, copper citrate, copper phthalate, copper tartrate, copper oleate, copper octylate, copper octenoate, copper naphthenate, and methacrylic acid.
• the salt include copper dimethyldithiocarbamate; examples of the salt of copper and an inorganic acid include copper nitrate; and copper chloride. Among these, copper carboxylate, copper ⁇ -diketone, and copper ⁇ -ketoester are preferred, and copper acetate and copper acetylacetone are more
• Vanadium compounds include vanadyl acetylacetonate, vanadium (III) naphthenate, vanadyl stearate, vanadium benzoylacetonate, bis(maltolate)oxovanadium(IV), oxobis(1-phenyl-1,3-butanedioate) Examples include vanadium (IV).
• the content of the reducing agent is preferably 10 parts by mass to 60 parts by mass, more preferably 15 parts by mass to 55 parts by mass, based on 100 parts by mass of the polymerization initiator. It is preferably 20 parts by mass to 50 parts by mass, and more preferably 20 parts by mass to 50 parts by mass.
• the content of the ascorbic acids in the polymerization initiator of the present disclosure is 10 parts by mass to 60 parts by mass based on 100 parts by mass of the polymerization initiator.
• the amount is preferably from 15 parts by weight to 55 parts by weight, and even more preferably from 20 parts by weight to 50 parts by weight.
• the content of the transition metal compound in the polymerization initiator of the present disclosure is 0.001 parts by mass to 1 part by mass based on 100 parts by mass of the polymerization initiator. It is preferably 0.0 part by weight, more preferably 0.005 part to 0.8 part by weight, and even more preferably 0.01 part to 0.7 part by weight.
• the curable composition preparation kit of the present disclosure includes a first agent containing a monomer (A) and a second agent containing a monomer (B), and at least one of the first agent and the second agent is as described above. or a polymerization accelerator, an oxidizing agent, and a reducing agent of the present disclosure, each independently.
• the first agent contains the monomer (A), and the second agent contains the monomer (B).
• Monomer (A) and monomer (B) may be the same monomer or different monomers.
• known monomers can be used as the monomer (A) and the monomer (B).
• Monomer (A) and monomer (B) may be monomers that do not contain acidic groups or may be monomers that contain acidic groups (hereinafter also referred to as "acidic group-containing monomers").
• Monomer (A) and monomer (B) preferably include monomers that do not contain acidic groups.
• the monomer is a monomer that undergoes a radical polymerization reaction and becomes a polymer due to the action of the aforementioned phosphonite compound or the polymerization accelerator, oxidizing agent, and reducing agent of the present disclosure.
• the number of monomers constituting the monomers in the present disclosure is not limited to one type, and two or more types may be used.
• Examples of monomers that do not contain acidic groups include (meth)acrylate monomers that do not contain acidic groups.
• Examples of (meth)acrylate monomers that do not contain acidic groups include monofunctional monomers, bifunctional monomers, and trifunctional or higher functional monomers.
• the monomer content i.e., the total amount of monomer (A) and monomer (B) in the curable composition to be prepared
• the monomer content is 10 It is preferably from 20% to 75% by weight, even more preferably from 30% to 60% by weight.
• Monomer monomers include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1,3-dihydroxypropyl (meth)acrylate, 2,3-dihydroxy
• An example is propyl (meth)acrylate.
• 2-hydroxyethyl methacrylate (HEMA) is preferred.
• aromatic compound-based difunctional monomers examples include 2,2-bis((meth)acryloyloxyphenyl)propane, 2,2-bis[4-(3-(meth)acryloyloxy)-2-hydroxypropoxy] phenyl]propane, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypolyethoxyphenyl)propane, 2,2-bis(4-( meth)acryloyloxypolypropoxyphenyl)propane, and the like.
• Bis-GMA 2,2-bis[4-(3-(methacryloyloxy)-2-hydroxypropoxyphenyl)propane
• Bis-GMA 2,2-bis(4-methacryloyloxypolyethoxyphenyl) Propane
• aliphatic compound-based difunctional monomers examples include erythritol di(meth)acrylate, sorbitol di(meth)acrylate, mannitol di(meth)acrylate, pentaerythritol di(meth)acrylate, and dipentaerythritol di(meth)acrylate.
• glycerol di(meth)acrylate ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl Glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate , 1,10-decanediol di(meth)acrylate, 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate (UDMA), 1,2-bis(3-methacryloyloxy-2-hydroxy) Examples include propyloxy)ethane.
• UDMA 2,2,4-trimethylhexam
• glycerol dimethacrylate triethylene glycol dimethacrylate (TEGDMA), 1,6-hexanediol dimethacrylate (HexDMA), neopentyl glycol dimethacrylate (NPG), 2,2,4-trimethylhexamethylene bis( 2-Carbamoyloxyethyl) dimethacrylate (UDMA) and 1,2-bis(3-methacryloyloxy-2-hydroxypropyloxy)ethane are preferred.
• TEGDMA triethylene glycol dimethacrylate
• HexDMA 1,6-hexanediol dimethacrylate
• NPG neopentyl glycol dimethacrylate
• UDMA 2,2,4-trimethylhexamethylene bis( 2-Carbamoyloxyethyl) dimethacrylate
• 1,2-bis(3-methacryloyloxy-2-hydroxypropyloxy)ethane are preferred.
• trifunctional or higher functional monomers examples include trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolmethane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate.
• acrylate dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, N,N-(2,2,4-trimethylhexamethylene)bis[2-( Examples include aminocarboxy)propane-1,3-diol]tetramethacrylate, 1,7-diacryloyloxy-2,2,6,6-tetraacryloyloxymethyl-4-oxyheptane, and the like.
• the above monomers may be blended singly or in combination of multiple types.
• the amount of the above-mentioned monomer not containing an acidic group is preferably in the range of 10 parts by mass to 100 parts by mass, and 20 parts by mass, based on 100 parts by mass of the total amount of monomer components in the curable composition preparation kit of the present disclosure.
• the range is more preferably 1 part to 100 parts by weight, and even more preferably 50 parts to 100 parts by weight.
• the monomer component in the kit for preparing a curable composition of the present disclosure includes an acidic group-containing monomer described below
• the amount of the monomer not containing an acidic group is the amount of the monomer component in the kit for preparing a curable composition of the present disclosure. It is preferably 10 parts by mass to 99 parts by mass, more preferably 30 parts by mass to 97 parts by mass, and even more preferably 50 parts by mass to 95 parts by mass, based on the total amount of 100 parts by mass.
• Monomer (A) and monomer (B) preferably contain a (meth)acrylic monomer (C) having a molecular weight of 100 to 5,000.
• the molecular weight of the (meth)acrylic monomer (C) is more preferably from 120 to 3,000, even more preferably from 150 to 2,000, particularly preferably from 200 to 1,000.
• the content of the (meth)acrylic monomer (C) relative to the total content of the monomer (A) and the monomer (B) is preferably 50% by mass or more, more preferably 70% by mass or more, and 90% by mass. % or more is more preferable.
• either the monomer (A) in the first agent or the monomer (B) in the second agent preferably contains an acidic group-containing monomer. Since at least one of the first agent and the second agent contains an acidic group-containing monomer, for example, when the curable composition preparation kit of the present disclosure is used for dental purposes, good tooth quality and dental prosthetic material can be obtained. It can provide high adhesion to.
• the monomer (A) in the first part preferably contains an acidic group-containing monomer, and the second part preferably contains ascorbic acids and a phosphonite compound.
• the monomer (A) in the first part contains an acidic group-containing monomer, and the second part does not contain an acidic group-containing monomer, and contains ascorbic acids and a phosphonite compound.
• the acidic group-containing monomer has at least one acidic group such as a phosphoric acid group, a pyrophosphoric acid group, a thiophosphoric acid group, a phosphonic acid group, a sulfonic acid group, a carboxylic acid group, and an acryloyl group, Examples include monomers containing at least one polymerizable group such as a methacryloyl group, a vinyl group, and a styrene group.
• the acidic group-containing monomer has an affinity with the adherend and has a demineralizing effect on the tooth substance.
• (meth)acryloyloxyalkyl dihydrogen phosphate such as 10-(meth)acryloyloxydecyl dihydrogen phosphate (MDP), bis[2-(meth)acryloyloxyethyl]hydrogen phosphate , bis[4-(meth)acryloyloxybutyl]hydrogen phosphate, bis[6-(meth)acryloyloxyhexyl]hydrogen phosphate, bis[8-(meth)acryloyloxyoctyl]hydrogen phosphate, bis[9- (meth)acryloyloxynonyl]hydrogen phosphate, bis[10-(meth)acryloyloxydecyl]hydrogen phosphate, 1,3-di(meth)acryloyloxypropyl dihydrogen phosphate, 2-(meth)acryloyloxyethyl Phenyl hydrogen phosphate, 2-(meth)acryloyloxyalkyl dihydrogen phosphate
• pyrophosphate group-containing monomers include bis[2-(meth)acryloyloxyethyl] pyrophosphate, bis[4-(meth)acryloyloxybutyl] pyrophosphate, and their acid chlorides, alkali metal salts, and ammonium salts. be done.
• thiophosphoric acid group-containing monomers examples include 2-(meth)acryloyloxyethyldihydrogenthiophosphate, 3-(meth)acryloyloxypropyldihydrogenthiophosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof. be done.
• Examples of phosphonic acid group-containing monomers include 2-(meth)acryloyloxyethyl phenylphosphonate, 5-(meth)acryloyloxypentyl-3-phosphonopropionate, and acid chlorides, alkali metal salts, and ammonium salts thereof. be done.
• sulfonic acid group-containing monomer examples include 2-(meth)acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, and 2-sulfoethyl (meth)acrylate.
• carboxylic acid group-containing monomers examples include monomers containing one carboxy group in the molecule and monomers containing multiple carboxy groups in the molecule.
• Monomers containing one carboxyl group in the molecule include (meth)acrylic acid, N-(meth)acryloylglycine, N-(meth)acryloyl aspartic acid, O-(meth)acryloyltyrosine, N-(meth)acryloyl Tyrosine, N-(meth)acryloylphenylalanine, N-(meth)acryloyl-p-aminobenzoic acid, N-(meth)acryloyl-o-aminobenzoic acid, p-vinylbenzoic acid, 2-(meth)acryloyloxybenzoic acid acid, 3-(meth)acryloyloxybenzoic acid, 4-(meth)acryloyloxybenzoic acid, N-(meth)acryloyl-5-aminosalicylic acid, N-(meth)acryloyl-4-aminosalicylic acid, 2-(meth)acryloyloxybenzoic acid, ) acryloy
• Examples of monomers containing multiple carboxyl groups in the molecule include 6-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 9-(meth)acryloyloxynonane-1,1-dicarboxylic acid, and 10-(meth)acryloyloxyhexane-1,1-dicarboxylic acid.
• 10-(meth)acryloyloxydecyl dihydrogen phosphate (MDP) and 1,3-di(meth)acryloyloxypropyl dihydrogen have high adhesive strength to adherends.
• the blending amount of the acidic group-containing monomer is preferably 1 part by mass to 50 parts by mass, and 3 parts by mass to 40 parts by mass, based on 100 parts by mass of the total amount of monomer components in the curable composition preparation kit of the present disclosure.
• the amount is more preferably 1 part by weight, and even more preferably 5 parts by weight to 30 parts by weight.
• the amount of the acidic group-containing monomer is 1 part by mass or more, it is easy to obtain high adhesiveness to various adherends. Further, when the amount of the acidic group-containing monomer is 50 parts by mass or less, it is easy to maintain a balance between polymerizability and adhesiveness.
• the total amount of monomer components means the total amount of the acidic group-containing monomer and the above-mentioned monomer not containing the acidic group.
• monomers in the present disclosure for example, monomers described in known documents such as WO 2012/157566, WO 2015/015220, WO 2015/015221, and JP 2016-094482 are used. be able to.
• At least one of the first agent and the second agent each independently contains the aforementioned phosphonite compound or the polymerization accelerator, oxidizing agent, and reducing agent of the present disclosure.
• Preferred embodiments of the above-mentioned phosphonite compound or the polymerization accelerator, oxidizing agent, and reducing agent of the present disclosure used in the curable composition preparation kit are as described above.
• the oxidizing agent preferably contains an organic peroxide, and the reducing agent preferably contains ascorbic acids and a transition metal compound. preferable.
• the first part preferably contains a transition metal compound and an organic peroxide
• the second part preferably contains an ascorbic acid and a phosphonite compound. is preferred.
• the total content of the phosphonite compounds contained in the first part and the second part is preferably 0.1% by mass to 5% by mass, and 0.2% by mass based on the total mass of the curable composition to be prepared. It is more preferably from 0.3% to 1% by weight, and even more preferably from 0.3% to 1% by weight.
• the total content of the phosphonite compounds contained in the first part and the second part is preferably 0.1% by mass to 1.5% by mass, based on the total mass of the curable composition to be prepared. It is more preferably from .1% by mass to 1% by mass, and even more preferably from 0.2% by mass to 0.5% by mass.
• the total content of the oxidizing agent contained in the first part and the second part is preferably 0.1% by mass to 10% by mass, and 0.3% by mass based on the total mass of the curable composition to be prepared. It is more preferably from 0.5% to 3% by weight, and even more preferably from 0.5% to 3% by weight.
• the total content of the reducing agent contained in the first agent and the second agent is preferably 0.2% by mass to 5% by mass, and 0.3% by mass based on the total mass of the curable composition to be prepared. It is more preferably 0.5% to 1.5% by weight, and even more preferably 0.5% to 1.5% by weight.
• the total content of ascorbic acid contained in the first part and the second part is preferably 0.2% by mass to 5% by mass, and 0.3% by mass based on the total mass of the curable composition to be prepared. It is more preferably 0.5% to 1.5% by weight, and even more preferably 0.5% to 1.5% by weight.
• the total content of the transition metal compound contained in the first part and the second part is preferably 0.0001% by mass to 0.1% by mass based on the total mass of the curable composition to be prepared, It is more preferably 0.0002% by mass to 0.05% by mass, and even more preferably 0.0003% by mass to 0.02% by mass.
• At least one of the first agent and the second agent may contain a filler, and it is preferable that the first agent and the second agent contain a filler.
• a filler may be used alone, or a combination of multiple types may be used.
• the filler include inorganic fillers, organic fillers, and composite fillers of inorganic fillers and organic fillers.
• inorganic fillers include silica; silica-based minerals such as kaolin, clay, mica, and mica; silica-based minerals such as Al 2 O 3 , B 2 O 3 , TiO 2 , ZrO 2 , BaO, and La; Examples include ceramics and glasses containing 2 O 3 , SrO, ZnO, CaO, P 2 O 5 , Li 2 O, Na 2 O, and the like.
• glasses lanthanum glass, barium glass, strontium glass, soda glass, lithium borosilicate glass, zinc glass, fluoroaluminosilicate glass, borosilicate glass, and bioglass are preferably used.
• Crystalline quartz, hydroxyapatite, alumina, titanium oxide, yttrium oxide, zirconia, calcium phosphate, barium sulfate, aluminum hydroxide, sodium fluoride, potassium fluoride, sodium monofluorophosphate, lithium fluoride, and ytterbium fluoride are also preferably used. It will be done.
• fine particle silica having a primary particle diameter of 0.001 ⁇ m to 0.1 ⁇ m is preferably used in terms of adhesive strength and ease of handling.
• organic fillers examples include polymethyl methacrylate, polyethyl methacrylate, polyfunctional methacrylate polymers, polyamide, polystyrene, polyvinyl chloride, chloroprene rubber, nitrile rubber, and styrene-butadiene rubber.
• composite fillers of inorganic fillers and organic fillers include those in which inorganic fillers are dispersed in organic fillers, and inorganic/organic composite fillers in which inorganic fillers are coated with various polymers.
• the filler may be used after being previously surface-treated with a known surface treatment agent such as a silane coupling agent.
• Surface treatment agents include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltri( ⁇ -methoxyethoxy)silane, ⁇ -methacryloyloxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - Examples include mercaptopropyltrimethoxysilane and ⁇ -aminopropyltriethoxysilane.
• the blending amount of the filler is preferably in the range of 10% by mass to 80% by mass, more preferably in the range of 30% by mass to 80% by mass, and more preferably in the range of 50% by mass to 75% by mass, based on the total mass of the curable composition of the present disclosure.
• a mass % range is more preferred.
• Non-conductive filler In the curable composition preparation kit of the present disclosure, it is preferable that at least one of the first agent and the second agent contains a non-conductive filler.
• a non-conductive filler means a filler having a resistance value of 1.00 ⁇ 10 ⁇ 4 ⁇ m or more. Although the upper limit of the resistance value of the non-conductive filler is not particularly limited, it may be, for example, 1.00 ⁇ 10 20 ⁇ m.
• Non-conductive filler examples include, for example, organic materials such as polyethylene, polystyrene, phenol resin, epoxy resin, acrylic resin, and benzoguanamine resin; silica (dimethylsilylated silica, etc.); silicates (borosilicate glass (barium borosilicate glass, etc.)); ), aluminosilicate glasses (boroaluminosilicate glass, strontium boroaluminosilicate glass, fluoroaluminosilicate glass, barium aluminosilicate glass, etc.)), ceramics, and inorganic materials such as boron nitride and barium nitride.
• organic materials such as polyethylene, polystyrene, phenol resin, epoxy resin, acrylic resin, and benzoguanamine resin
• silica dimethylsilylated silica, etc.
• silicates borosilicate glass (barium borosilicate glass, etc.)
• aluminosilicate glasses
• silica and silicates are preferable, and dimethylsilylated silica and barium aluminosilicate are more preferable as materials for the non-conductive filler.
• the first part contains a non-conductive filler, and the content of the non-conductive filler relative to the total mass of the first part is preferably 10% by mass or more, more preferably 20% by mass or more, More preferably, it is 30% by mass or more.
• the second part contains a non-conductive filler
• the second part contains the non-conductive filler
• the content of the non-conductive filler with respect to the total mass of the second part is 10% by mass or more.
• the content is preferably 20% by mass or more, more preferably 30% by mass or more.
• the content of the non-conductive filler is 10% by mass or more based on the total mass of the first component, and the non-conductive filler is When a conductive filler is included in the second part, it is preferable that the content of the non-conductive filler is 10% by mass or more based on the total mass of the second part.
• the curable composition of the present disclosure may contain additives such as a photopolymerization initiator, a stabilizer (polymerization inhibitor), a colorant, a fluorescent agent, and an ultraviolet absorber.
• a photopolymerization initiator known photopolymerization initiators can be used, such as camphorquinone (CQ), ethyl dimethylaminobenzoate (EDB), and 2-butoxyethyl 4-(dimethylamino)benzoate (BEDB). ) etc.
• CQ camphorquinone
• EDB ethyl dimethylaminobenzoate
• BEDB 2-butoxyethyl 4-(dimethylamino)benzoate
• antibacterial substances such as cetylpyridinium chloride, benzalkonium chloride, (meth)acryloyloxydodecylpyridinium bromide, (meth)acryloyloxyhexadecylpyridinium chloride, (meth)acryloyloxydecyl ammonium chloride, and triclosan may be added. good.
• Known dyes and pigments may be added to the curable composition of the present disclosure.
• the curable composition preparation kit of the present disclosure is preferably used for dental materials.
• dental materials include, but are not limited to, dental adhesives, dental filling materials, dental sealants (tooth fissure sealants), abutment building materials, denture base resins, and denture base lining materials. , dental crown prosthesis resins (hard resins for dental crowns), dental room temperature polymerization resins, and the like.
• the curable composition preparation kit of the present disclosure is particularly preferably used as a dental adhesive.
• dental adhesives include dental adhesive resin cement, orthodontic adhesives, adhesives for fixing loose teeth, cavity coating adhesives, and dental bonding materials. Cement is preferred.
• dental filling materials include dental composite resins (including dental self-adhesive composite resins), root canal filling materials, temporary sealants, backing materials, and the like.
• the kit for preparing a curable composition of the present disclosure may be used for dental treatment.
• the dental treatment method of the present disclosure includes a step of mixing the first agent and the second agent in the curable composition preparation kit of the present disclosure to obtain a curable composition, and administering the curable composition in the oral cavity.
• the method may also include a step of polymerizing to obtain a cured product.
• the step of mixing the first agent and the second agent to obtain a curable composition may be performed within the oral cavity or outside the oral cavity.
• the obtained curable composition may be applied to the oral cavity and polymerized within the oral cavity to obtain a cured product.
• the method including the step of polymerizing in the oral cavity to obtain a cured product is suitable, for example, when the curable composition preparation kit is used for dental adhesive resin cement, composite resin for filling and restoration, etc.
• the dental treatment method of the present disclosure may include a step of polymerizing the curable composition of the present disclosure outside the oral cavity to obtain a cured product, and a step of applying the cured product into the oral cavity.
• the step of polymerizing outside the oral cavity to obtain a cured product may be a step of polymerizing the curable composition in a cast mold to obtain a cured product.
• the cured product obtained outside the oral cavity may be processed as necessary, and the cured product after processing may be applied inside the oral cavity.
• the method of obtaining a cured product by polymerizing outside the oral cavity is suitable, for example, when the cured product is used for CAD/CAM resin blocks, temporary crowns, artificial teeth, etc.
• the curable composition of the present disclosure includes the aforementioned phosphonite compound or the polymerization accelerator of the present disclosure, an oxidizing agent, a reducing agent, and a monomer.
• the curable composition of the present disclosure includes the above configuration, polymerizability can be favorably improved.
• Specific examples, preferred embodiments, etc. of the monomer in the curable composition are the same as those of the above-mentioned monomer.
• the curable composition of the present disclosure preferably further includes a non-conductive filler. Specific examples, preferred embodiments, etc. of the non-conductive filler in the curable composition are the same as those for the above-mentioned non-conductive filler.
• the cured product of the present disclosure is a cured product of the curable composition of the present disclosure, or a cured product obtained using the curable composition preparation kit of the present disclosure.
• the cured product of the present disclosure can be suitably used as a dental material. That is, the dental material of the present disclosure preferably includes the cured product of the present disclosure.
• the obtained reaction product was extracted. Specifically, an equal amount of distilled water was added to the reaction solution, then an equal amount of diethyl ether was added, and the mixture was extracted and washed using a separating funnel. After repeating the above extraction three times, an equal amount of distilled water was added to the obtained organic layer and washed with a separatory funnel. After repeating the above washing three times, the resulting organic layer was dried by adding sodium sulfate, and then concentrated under reduced pressure. The obtained crude product was washed with a hexane/ethyl acetate solvent, and separated and purified by filtration.
• Example 1 As shown in Table 1, the first and second parts of Example 1 and Comparative Examples 1 to 3 were prepared using each component.
• the numbers in each component column mean the amount (parts by mass) of each component in the first agent or the second agent.
• Example 1 As shown in Table 1, in Example 1, the evaluation of polymerizability was better than in Comparative Examples 1 to 3 by using a phosphonite compound.

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• 2023
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