WO2022209203A1 - 歯科用組成物の製造方法、及び歯科用組成物 - Google Patents
歯科用組成物の製造方法、及び歯科用組成物 Download PDFInfo
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- WO2022209203A1 WO2022209203A1 PCT/JP2022/002288 JP2022002288W WO2022209203A1 WO 2022209203 A1 WO2022209203 A1 WO 2022209203A1 JP 2022002288 W JP2022002288 W JP 2022002288W WO 2022209203 A1 WO2022209203 A1 WO 2022209203A1
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- polymerizable monomer
- dental composition
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- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- KSOMQZOHPWJPMM-UHFFFAOYSA-N propyl 4-(diethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(CC)CC)C=C1 KSOMQZOHPWJPMM-UHFFFAOYSA-N 0.000 description 1
- SCNYCWQULCHALD-UHFFFAOYSA-N propyl 4-(dimethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(C)C)C=C1 SCNYCWQULCHALD-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 1
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
-
- 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
- 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 method for producing a dental composition and a dental composition.
- dental composite resins are widely used because they contain a photopolymerization initiator so that they can be polymerized and cured in a timely manner by light irradiation (see, for example, Patent Documents 1 and 2).
- the highly light-scattering composite resin incorporates the color of the natural teeth around the filling area, so it has good color matching and excellent aesthetics.
- An object of the present invention is to provide a dental composition that provides a highly light-scattering hardened product and is excellent in operability.
- One aspect of the present invention is a method of making a dental composition having a second component dispersed within a first component, wherein the first component is a liquid. a paste containing a polymerizable monomer, the second component contains a solvent in which the first polymerizable monomer is insoluble, and a step of mixing the first component and the second component include.
- FIG. 1 is an optical micrograph of a dental composition according to an embodiment before hardening.
- 4 is a photograph showing the appearance after curing of the dental composition according to the embodiment.
- the method for producing a dental composition according to this embodiment is a method for producing a dental composition in which the second component is dispersed in the first component.
- the method for producing the dental composition of the present embodiment includes a step of mixing the first component and the second component (hereinafter referred to as mixing step).
- the first component is a paste containing a liquid first polymerizable monomer.
- paste indicates a pasty liquid.
- the liquid first polymerizable monomer is, for example, liquid at normal temperature and normal pressure.
- the first polymerizable monomer is insoluble in the below-described first solvent.
- the first polymerizable monomer is not particularly limited, for example, it is preferably a (meth)acrylate, and it is further a polyfunctional (meth)acrylate having two or more (meth)acryloyloxy groups. preferable.
- Examples of the first polymerizable monomer include ethoxylated bisphenol A dimethacrylate, neopentyl glycol dimethacrylate, urethane dimethacrylate, glycerin dimethacrylate, triethylene glycol dimethacrylate, tricyclodecanedimethanol dimethacrylate, and the like. be done. These first polymerizable monomers may be used singly or in combination of two or more.
- the content of the first polymerizable monomer in the dental composition is not particularly limited, but is preferably 1% by mass or more and 99.9% by mass or less, more preferably 1.5% by mass. 79 mass % or less, more preferably 2 mass % or more and 49 mass % or less.
- the content of the first polymerizable monomer in the dental composition is 1% by mass or more, the mechanical strength of the cured product of the dental composition is improved, and when it is 99.9% by mass or less. , the function or performance derived from the second polymerizable monomer of the cured product of the dental composition is improved.
- the first component preferably further contains a hydrophobic filler.
- hydrophobic fillers examples include silane-treated glass fillers.
- the silane-treated glass filler is, for example, barium glass treated with 3-methacryloyloxypropyltrimethoxysilane. These hydrophobic fillers may be used individually by 1 type, and may use 2 or more types together.
- the blending amount of the hydrophobic filler in the dental composition is, for example, preferably 45% by mass or more and 75% by mass or less, more preferably 50% by mass or more and 70% by mass or less, still more preferably 55% by mass or more and 65% by mass. % by mass or less.
- amount of the hydrophobic filler in the dental composition is 45% by mass or more, the mechanical strength of the cured product of the dental composition is improved. and the operability of the dental composition can be improved.
- the first component may contain inorganic fillers other than hydrophobic fillers as other components.
- inorganic fillers examples include silicic anhydride powder, fumed silica, alumina powder, glass powder (eg, barium glass powder, fluoroaluminosilicate glass powder), and the like. These inorganic fillers may be treated with a surface treatment agent such as a silane coupling agent. These inorganic fillers may be used individually by 1 type, and may use 2 or more types together.
- the content of the inorganic filler in the dental composition is, for example, preferably 0.01% by mass or more and 30% by mass or less, more preferably 0.05% by mass or more and 20% by mass or less, and even more preferably 0.05% by mass or more and 20% by mass or less. It is 1 mass % or more and 10 mass % or less.
- the amount of the inorganic filler in the dental composition is 0.01% by mass or more and 30% by mass or less, the viscosity of the dental composition containing the glass is lowered, and the operability of the dental composition is improved. be able to.
- an automatic mortar for mixing in the production of the paste-like first component.
- an automatic mortar is unnecessary, and a rotation-revolution mixer or the like may be used.
- the second component contains a first solvent in which the first polymerizable monomer described above is insoluble.
- insoluble means that the amount of the first polymerizable monomer that dissolves in 100 g of solvent at 25° C. is less than 1 g.
- the first solvent is a solvent in which the first polymerizable monomer is insoluble.
- the first solvent is an example of a solvent insoluble in the first polymerizable monomer in the method for producing a dental composition of the present embodiment.
- the first solvent is not particularly limited as long as it is a solvent in which the first polymerizable monomer is insoluble. is mentioned. These first solvents may be used alone or in combination of two or more.
- the content of the first solvent in the dental composition is not particularly limited. Below, it is more preferably 0.03% by mass or more and 30% by mass or less.
- the content of the first solvent in the dental composition is 0.01% by mass or more, the function or performance derived from the second polymerizable monomer of the cured product of the dental composition is improved, When the content is 40% by mass or less, the light scattering properties and operability of the cured dental composition are improved.
- the second component preferably further contains a second polymerizable monomer that is solid.
- the solid second polymerizable monomer is solid at normal temperature and normal pressure, and is soluble in the first solvent described above. Soluble means that 10 g or more of the second polymerizable monomer dissolves in 100 g of solvent at 25°C. Also, the second polymerizable monomer is preferably insoluble in the first polymerizable monomer.
- the second polymerizable monomer is preferably a (meth)acrylate, more preferably a monofunctional (meth)acrylate having one (meth)acryloyloxy group.
- the content of the second polymerizable monomer in the dental composition is not particularly limited, but is preferably 0.01% by mass or more and 99% by mass or less, more preferably 0.02% by mass. 79 mass % or less, more preferably 0.03 mass % or more and 49 mass % or less.
- the content of the second polymerizable monomer in the dental composition is 0.01% by mass or more, the function or performance derived from the second polymerizable monomer of the cured product of the dental composition When the amount is 99% by mass or less, the light scattering properties and operability of the cured dental composition are improved.
- the second polymerizable monomer When the first solvent is water, the second polymerizable monomer may be dissolved in water by causing the second polymerizable monomer to absorb moisture in the atmosphere.
- the content of the first solvent in the dental composition is not particularly limited. Below, it is more preferably 0.03% by mass or more and 30% by mass or less.
- the content of the first solvent in the dental composition is 0.01% by mass or more, the function or performance derived from the second polymerizable monomer of the cured product of the dental composition is improved, When the content is 40% by mass or less, the light scattering properties and operability of the cured dental composition are improved.
- the mass ratio of the first solvent to the second polymerizable monomer is preferably 0.01 or more and 5 or less, more preferably 0.1 or more and 2 or less.
- the mass ratio of the first solvent to the second polymerizable monomer is 0.01 or more, the stability when the second polymerizable monomer is dissolved in the first solvent is improved, When it is 5 or less, the mechanical strength of the hardened dental composition is improved.
- the mass ratio of the first polymerizable monomer to the total amount of the second polymerizable monomer and the first solvent is preferably 0.1 or more and 100 or less, and is 0.5 or more and 50 or less. is more preferred.
- the mass ratio of the first polymerizable monomer to the total amount of the second polymerizable monomer and the first solvent is 0.1 or more, the mechanical strength of the cured dental composition is improved. , 100 or less, the performance derived from the second polymerizable monomer of the cured product of the dental composition is improved.
- the paste-like first component containing the liquid first polymerizable monomer and the first polymerizable monomer are By mixing the second component containing the insoluble first solvent, the dispersibility of the second component in the first component can be controlled. Thereby, the second component can be uniformly localized in the first component.
- the method for producing a dental composition of the present embodiment when the dental composition hardens, the first component and the second component are in a state similar to a composite filler, and light scattering properties are obtained. Therefore, according to the present embodiment, it is possible to obtain a dental composition having a cured product with excellent light scattering properties.
- a cured product with high light scattering properties can be obtained as described above without blending a conventional organic-inorganic composite filler. Therefore, according to the present embodiment, it is possible to prevent deterioration in operability due to the addition of a conventional organic-inorganic composite filler.
- the first component contains a hydrophobic filler, it is possible to improve the dispersibility of the first component, which is a paste. Moreover, by mixing such a first component with the second component, the dispersibility of the dental composition can be improved. Furthermore, by containing such a hydrophobic filler, the first component can improve the light scattering properties of the cured product without deteriorating the operability.
- the second component contains the solid second polymerizable monomer, and when the first component is mixed with such a second component, the first , the second polymerizable monomer, and the first solvent are mixed.
- the particle size of the second polymerizable monomer can be controlled. Due to the difficulty, the second polymerizable monomer cannot be uniformly localized in the first polymerizable monomer. As a result, the appearance and strength of the hardened dental composition are reduced.
- the second polymerizable monomer becomes the first polymerizable monomer Since it functions as a filler having a polarity different from that of the body, the viscosity of the dental composition is significantly increased, and the operability of the dental composition is reduced.
- a paste-like first polymerizable monomer that is insoluble in the first solvent, a second polymerizable monomer that is soluble in the first solvent, and the first By mixing the solvent, the second polymerizable monomer can be uniformly localized in the dental composition.
- the dental composition that is excellent in light scattering properties and that does not easily deteriorate in operability while imparting the function or performance derived from the second polymerizable monomer to the cured product of the dental composition.
- the second component contains the second polymerizable monomer soluble in the first solvent
- the second polymerizable monomer in the dental composition can function as a filler having a polarity different from that of the first polymerizable monomer. Therefore, in the present embodiment, the presence of such a second polymerizable monomer can prevent deterioration of the light scattering properties due to changes during storage of the dental composition.
- the second polymerizable monomer preferably has a functional group exhibiting at least one of antibacterial and antiviral properties.
- the functional group that exhibits at least one of antibacterial and antiviral properties means that when one functional group exhibits both antibacterial and antiviral properties, one functional group exhibits either antibacterial or antiviral properties. Indicates when to indicate.
- the functional group exhibiting antibacterial and antiviral properties includes the case of having both a functional group exhibiting antibacterial properties and a functional group exhibiting antiviral properties.
- the functional group that exhibits at least one of antibacterial and antiviral properties is not particularly limited, but includes, for example, a quaternary ammonium base.
- the quaternary ammonium base can function as a functional group exhibiting antibacterial properties (hereinafter referred to as an antimicrobial group) and can also function as a functional group exhibiting antiviral properties (hereinafter referred to as an antiviral group).
- Examples of the second polymerizable monomer having a functional group exhibiting at least one of antibacterial and antiviral properties include 2-(methacryloyloxy)ethyltrimethylammonium chloride, (3-acrylamidopropyl)trimethylammonium chloride, ( 2-(Acryloyloxy)ethyl)trimethylammonium chloride, N-(2-acryloyloxyethyl)-N-benzyl-N,N-dimethylammonium chloride, dimethylaminopropylacrylamide methyl chloride quaternary salt, dimethylaminoethyl acrylate methyl chloride Quaternary salts, monofunctional polymerizable monomers such as dimethylaminoethyl acrylate benzyl chloride quaternary salts, diallyl-type quaternary ammonium salts such as diallyldimethylammonium chloride and diallyldiethylammonium chloride, and the following chemical formulas
- polymerizable monomers such as compounds represented by the above.
- These second polymerizable monomers having a functional group exhibiting at least one of antibacterial and antiviral properties may be used singly or in combination of two or more.
- Examples of the second polymerizable monomer having neither an antibacterial group nor an antiviral group include phenoxyethylene glycol methacrylate and dimethylaminoethyl methacrylate.
- These second polymerizable monomers having neither an antibacterial group nor an antiviral group may be used singly or in combination of two or more.
- the second polymerizable monomer when the second polymerizable monomer has an antibacterial group, imparting antibacterial properties as a function or performance derived from the second polymerizable monomer to the cured product of the dental composition. can be done.
- antiviral properties when the second polymerizable monomer has an antiviral group, antiviral properties can be imparted to the cured product of the dental composition as a function or performance derived from the second polymerizable monomer. can.
- a surfactant may be added when mixing the first polymerizable monomer, the second polymerizable monomer, and the first solvent, or the surfactant may be No need to add.
- the surfactant is not particularly limited as long as it can improve the dispersibility of the solution, but examples include sodium lauryl sulfate, glycerin fatty acid ester, and the like. These surfactants may be used alone or in combination of two or more.
- a photopolymerization initiator it is preferable to add and knead a photopolymerization initiator, a tertiary amine, a polymerization inhibitor, etc. as other components in the mixing step.
- photopolymerization initiators include camphorquinone, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzyl ketal, diacetyl ketal, benzyl dimethyl ketal, benzyl Diethyl ketal, benzyl bis(2-methoxyethyl) ketal, 4,4′-dimethyl (benzyl dimethyl ketal), anthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 1,2-benzanthraquinone, 1-hydroxyanthraquinone, 1- Methylanthraquinone, 2-ethylanthraquinone, 1-bromoanthraquinone, thioxanthone, 2-isopropylthioxanthone, 2-nitrothioxanthone, 2-methyl
- the tertiary amine may be either a tertiary aliphatic amine or a tertiary aromatic amine, but is preferably a tertiary aromatic amine, and is an alkyl p-dialkylaminobenzoate. is more preferred.
- tertiary aliphatic amines examples include N,N-dimethylaminoethyl methacrylate and triethanolamine.
- alkyl p-dialkylaminobenzoate examples include methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate, propyl p-dimethylaminobenzoate, amyl p-dimethylaminobenzoate, and p-dimethylaminobenzoic acid.
- alkyl p-dialkylaminobenzoate examples include methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate, propyl p-dimethylaminobenzoate, amyl p-dimethylaminobenzoate, and p-dimethylaminobenzoic acid.
- examples include isoamyl, ethyl p-diethylaminobenzoate, propyl p-diethylaminobenzoate and the like.
- tertiary aromatic amines other than alkyl p-dialkylaminobenzoate include 7-dimethylamino-4-methylcoumarin, N,N-dimethylaniline, N,N-dibenzylaniline, N,N-dimethyl -p-toluidine, N,N-diethyl-p-toluidine, N,N-bis(2-hydroxyethyl)-p-toluidine, N,N,2,4,6-pentamethylaniline, N,N,2 ,4-tetramethylaniline, N,N-diethyl-2,4,6-trimethylaniline and the like.
- tertiary amines may be used singly or in combination of two or more.
- polymerization inhibitors examples include dibutylhydroxytoluene (2,6-di-tert-butyl-p-cresol) and 6-tert-butyl-2,4-xylenol. These polymerization inhibitors may be used alone or in combination of two or more.
- the mixing step may include a step of dissolving the second polymerizable monomer in the first solvent to obtain a solution, and a step of mixing the solution and the first component.
- the second polymerizable monomer is formed in the dental composition.
- Monomers can be localized more uniformly. As a result, it is possible to further improve the light scattering properties and operability of the cured dental composition while imparting the function or performance derived from the second polymerizable monomer to the cured dental composition. can.
- the second polymerizable monomer has an antibacterial group
- antibacterial properties can be imparted to the cured dental composition.
- antiviral properties can be imparted to the hardened dental composition.
- the A method of kneading the solution and the first component a method of mixing the solution and the first component using a magnetic stirrer, and a stirrer having a stirring blade to mix the solution and the first component. and the like.
- the mixing step includes dissolving at least part of the first polymerizable monomer and the second polymerizable monomer in a second solvent to obtain a solution, and removing the second solvent from the solution. distilling off to obtain a dispersion in which the second polymerizable monomer is dispersed in at least part of the first polymerizable monomer; and mixing.
- the second solvent is not particularly limited, and examples thereof include organic solvents such as ethanol, acetone, and hexane. These second solvents may be used singly or in combination of two or more.
- the content of the second solvent in the solution is not particularly limited, it is preferably 10% by mass or more and 99% by mass or less, for example.
- the content of the second solvent in the solution is 10% by mass or more, the dissolution stability of the polymerizable monomer is improved, and when it is 99% by mass or less, the second solvent is distilled off from the solution. easier.
- the second polymer when a dispersion liquid in which the second polymerizable monomer is dispersed in the first polymerizable monomer is mixed with the first solvent, the second polymer is added to the dental composition.
- of polymerizable monomers can be more uniformly localized.
- the appearance and strength of the cured dental composition can be further improved while imparting the function or performance derived from the second polymerizable monomer to the cured dental composition.
- the second polymerizable monomer has an antibacterial group
- antibacterial properties can be imparted to the cured dental composition.
- antiviral properties can be imparted to the hardened dental composition.
- the timing of mixing the dispersion and the remainder of the first polymerizable monomer is not particularly limited, but when mixing the dispersion and the first solvent, the first polymerizable monomer is preferably mixed with the remainder of the first polymerizable monomer
- the mass ratio of the second polymerizable monomer to at least part of the first polymerizable monomer when obtaining the solution is preferably 0.01 or more and 100 or less, and 0.05 or more and 50 or less. It is even more preferable to have When the mass ratio of the first polymerizable monomer and the second polymerizable monomer is 0.01 or more and 100 or less, the dispersion state of the dispersion obtained by distilling off the second solvent from the solution is become good.
- Methods of mixing the dispersion and the first solvent include, for example, a method of stirring the dispersion and the first solvent, a method of mixing the dispersion and the first solvent using a magnetic stirrer, A method of mixing the dispersion liquid and the first solvent using a stirrer having a stirring blade can be used.
- a surfactant may or may not be added when mixing the dispersion and the first solvent.
- the surfactant is not particularly limited as long as it can improve the dispersibility of the solution, but examples include sodium lauryl sulfate, glycerin fatty acid ester, and the like. These surfactants may be used alone or in combination of two or more.
- the above-mentioned hydrophobic filler, inorganic filler, photopolymerization initiator, tertiary amine, polymerization inhibitor, etc. are added as other components. Kneading is preferred.
- the dental composition of this embodiment has the second component dispersed in the first component.
- the first component is a paste containing a liquid first polymerizable monomer
- the second component contains a solvent in which the first polymerizable monomer is insoluble.
- the dental composition of this embodiment can be produced by the method for producing a dental composition described above.
- the first component used in the dental composition of the present embodiment the first component used in the method for producing the dental composition described above can be used.
- the first polymerizable monomer the first polymerizable monomer used in the above-described method for producing a dental composition can be used.
- the second component used in the above-described method for producing a dental composition can be used as the second component used in the dental composition of the present embodiment.
- the first solvent used in the above-described method for producing a dental composition can be used as the solvent used in the dental composition of the present embodiment.
- the content of the first polymerizable monomer in the dental composition is not particularly limited, but is preferably 1% by mass or more and 99.9% by mass or less, more preferably 1.5% by mass. 79 mass % or less, more preferably 2 mass % or more and 49 mass % or less.
- the content of the first solvent in the dental composition is not particularly limited. Below, it is more preferably 0.03% by mass or more and 30% by mass or less.
- the dental composition according to the present embodiment includes a pasty first component containing a liquid first polymerizable monomer, and a first solvent in which the first polymerizable monomer is insoluble.
- the second component By including the second component, the same effect as the dental composition obtained by the above-described manufacturing method can be obtained.
- the dispersibility of the second component in the first component is controlled, and the second component is uniformly localized in the first component. be able to.
- the dental composition of the present embodiment when the dental composition is cured, the first component and the second component are in a state similar to a composite filler, and light scattering is obtained.
- the dental composition of the present embodiment can be a cured product with excellent light scattering properties.
- a cured product with high light scattering properties can be obtained without blending conventional organic-inorganic composite fillers. Therefore, in the dental composition of the present embodiment, it is possible to prevent deterioration in operability due to the addition of a conventional organic-inorganic composite filler.
- the second component preferably further contains a second polymerizable monomer that is solid.
- the second polymerizable monomer is preferably soluble in the first solvent described above.
- the second polymerizable monomer the second polymerizable monomer used in the above-described method for producing a dental composition can be used.
- the content of the second polymerizable monomer in the dental composition is not particularly limited, but is preferably 0.01% by mass or more and 99% by mass or less, more preferably 0.02% by mass. 79 mass % or less, more preferably 0.03 mass % or more and 49 mass % or less.
- the same effects as those of the dental composition obtained by the above-described manufacturing method can be obtained.
- a pasty first polymerizable monomer that is insoluble in a first solvent and a second polymerizable monomer that is soluble in the first solvent The second polymerizable monomer can be uniformly localized in the dental composition when the body and the first solvent are mixed.
- the function or performance derived from the second polymerizable monomer is imparted to the cured product of the dental composition, the light scattering property is excellent, and the operability is reduced. It can be a difficult dental composition.
- the second polymerizable monomer preferably has a functional group exhibiting at least one of antibacterial and antiviral properties.
- the second polymerizable monomer having a functional group exhibiting at least one of antibacterial and antiviral properties includes an antibacterial group and/or an antiviral group used in the above-described method for producing a dental composition. It is possible to use a second polymerizable monomer having
- the antibacterial group and/or antiviral group used in the second polymerizable monomer can be the quaternary ammonium base used in the above-described method for producing a dental composition, or the like. .
- the second polymerizable monomer when the second polymerizable monomer has an antibacterial group and/or an antiviral group, the second polymerizable monomer has an antibacterial group.
- antibacterial properties can be imparted to the hardened dental composition as a function or performance derived from the second polymerizable monomer.
- antiviral properties when the second polymerizable monomer has an antiviral group, antiviral properties can be imparted to the cured product of the dental composition as a function or performance derived from the second polymerizable monomer. can.
- the use of the dental composition of the present embodiment is not particularly limited, and the dental composition of the present embodiment is used for, for example, dental composite resins, dental cements, denture base resins, general-purpose dental resins, and the like. be able to.
- the dental composition of the present embodiment can be preferably used for dental composite resins, among others, from the viewpoint that it can be a dental composition that has excellent light scattering properties and is less likely to deteriorate in operability. , and more preferably for flowable composite resins.
- the dental composition of the present embodiment is used for a flowable composite resin
- the flowable composite resin may be of a one-pack type or a two-pack type.
- the extrusion hardness of the flowable composite resin can usually be 10 kgf or less. Thereby, the shapeability and operability of the flowable composite resin can be improved.
- the mode of providing the flowable composite resin is not particularly limited.
- the inner diameter of the needle of the needle tip can be 0.3 mm or more and 0.9 mm or less.
- the package has, for example, two syringes connected in parallel and two plungers connected in parallel, and at the tips of both syringes, A static mixer may be provided.
- the dental composition of the present embodiment can impart antibacterial and/or antiviral properties as a function or performance derived from the second polymerizable monomer to the cured product of the dental composition. From the point of view, it is suitably used for products in the dental field that require performance such as antibacterial and antiviral properties.
- Aerosil R812 fine particle silica surface-treated with hexamethyldisilazane, manufactured by Nippon Aerosil Co., Ltd., AEROSIL (registered trademark) R812
- BPE-80N bisphenol A polyethoxymethacrylate
- NPG neopentyl glycol dimethacrylate
- DCP tricyclodecanedimethanol dimethacrylate
- CQ camphorquinone
- EPA ethyl p-dimethylaminobenzoate
- BHT 6-tert-dibutyl-2,4-
- MTMAC 2-(methacryloyloxy)ethyltrimethylammonium chloride
- DADMAC diallyldimethylammonium chloride
- UDMA di-2-methacryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbamate
- the refractive index of each component contained in the original solution is 1.543 for BPE-80N, 1.452 for NPG, 1.500 for DCP, 1.460 for MTMAC, 1.480 for DADMAC, and 1.480 for water.
- barium glass manufactured by SCHOTT, G018-053 is 1.53
- silicon dioxide SiO 2
- the silane-treated glass filler is 3-methacryloyloxypropyltrimethoxysilane with a weight ratio of 8 w/w% to the glass, barium glass powder (G018-053 UF 0.4 ⁇ m, manufactured by SCHOTT) and silane. It has been processed.
- the silane treatment method was performed with reference to Patent Document 2 (Japanese Patent No. 6793241) of the prior art document.
- the organic filler is an organic-inorganic composite filler produced with reference to JP-A-2011-68596.
- this organic-inorganic composite filler includes Si 2 O, SrO, B 2 O 3 , BaO, Al 2 O 3 , Na 2 O, CaO, ZnO, La 2 O 3 , WO 3 , ZrO 2 , TiO 2 , Nb 2 O 5 , F or the like as the main component, mixed with a (meth)acrylate compound, polymerized and cured, and pulverized.
- ⁇ Light scattering properties> The resulting flowable composite resin paste was evenly applied to the surface of an acrylic plate to prepare a disk-shaped test piece with a diameter of 15 mm and a thickness of 1 mm (Figs. 1 and 2). Using Light Prima II Plus), both sides of the test piece were irradiated for 10 seconds 9 times each to prepare a cured body, which was used as a test body (Fig. 3). Using a goniophotometer (manufactured by Murakami Color Research Laboratory), the light scattering properties (light scattering properties) were evaluated under conditions of a measurement range of ⁇ 90. Evaluation criteria are as follows. Good: The measurement angle at which the transmitted light intensity becomes 10% or less for the first time is outside the range of ⁇ 30.
- Transparency was evaluated by measuring the total light transmittance (T.T) of the specimen (Fig. 3) obtained in the above light scattering property test using a haze meter (manufactured by Nippon Denshoku Industries Co., Ltd.). did. Transparency was evaluated as good (having transparency) when the total light transmittance (T.T) was 35% or more.
- Examples 1 to 6 had good light scattering properties, transparency, and paste fluidity. Among them, Examples 1 to 3 were more aesthetically pleasing.
- Comparative Example 1 was unsuccessful in light scattering, and Comparative Example 2 was unsatisfactory in paste fluidity.
- Example 1 in the uncured flowable composite resin 20 fixed to the acrylic plate (object) 10, the second polymerizable monomer is included in the first polymerizable monomer 30. It is considered that the solution 40 dissolved in the solvent is uniformly dispersed (the droplet size of the solution 40 in which the second polymerizable monomer is dissolved in the first solvent is fine) (Fig. 1, See Figure 2).
- Acrylic plate (object) 20 flowable composite resin 30 first polymerizable monomer 40 solution in which second polymerizable monomer is dissolved in first solvent
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Abstract
Description
本実施形態に係る歯科用組成物の製造方法は、第1の成分の中に、第2の成分が分散している歯科用組成物を製造する方法である。本実施形態の歯科用組成物の製造方法は、第1の成分と、第2の成分と、を混合する工程(以下、混合工程という)を含む。
第1の成分は、液体である第1の重合性単量体を含むペーストである。本明細書において、ペーストとは、ペースト状の液体を示す。
液体である第1の重合性単量体は、例えば、常温常圧で液体である。第1の重合性単量体は、後述する第1の溶媒に不溶である。
第2の成分は、上述の第1の重合性単量体が不溶な第1の溶媒を含む。本明細書において、不溶とは、25℃において、溶媒100gに溶解する第1の重合性単量体の量が1g未満であることを示す。
第1の溶媒は、第1の重合性単量体が不溶な溶媒である。本明細書において、第1の溶媒は、本実施形態の歯科用組成物の製造方法における第1の重合性単量体が不溶な溶媒の一例である。
固体である第2の重合性単量体は、常温常圧で固体であり、上述の第1の溶媒に可溶である。可溶とは、25℃で、溶媒100gに第2の重合性単量体が10g以上溶解することを示す。また、第2の重合性単量体は、第1の重合性単量体に不溶であることが好ましい。
で表される化合物等の多官能の重合性単量体等が挙げられる。抗菌性及び抗ウイルス性の少なくとも一方を示す官能基を有するこれらの第2の重合性単量体は、1種を単独で使用してもよいし、2種以上を併用してもよい。
第2の溶媒としては、特に限定されず、例えば、エタノール、アセトン、ヘキサン等の有機溶媒等が挙げられる。これらの第2の溶媒は、1種を単独で使用してもよく、2種以上を併用してもよい。
本実施形態の歯科用組成物は、第1の成分の中に、第2の成分が分散している。ここで、第1の成分は、液体である第1の重合性単量体を含むペーストであり、第2の成分は、第1の重合性単量体が不溶な溶媒を含む。
重合性モノマー成分として、ビスフェノールAポリエトキシメタクリレート(BPE-80N)120g、ネオペンチルグリコールジメタクリレート(NPG)30g、トリシクロデカンジメタノールジメタクリレート(DCP)30gをそれぞれ計量し、次いで、カンファーキノン(CQ)1.5g、p-ジメチルアミノ安息香酸エチル(EPA)3.0g、6-tert-ジブチル-2,4-キシレノール(BHT)1.2gを加え、スターラーを用いて均一に混錬し、元液を調製した。
先に調製した元液を3.5g計量し、アエロジルR812(ヘキサメチルジシラザンで表面処理された微粒子シリカ、日本アエロジル社製、AEROSIL(登録商標)R812)0.16g計量して加え、自動乳鉢を用いて混錬した。5分間混錬した後に、シラン処理ガラスフィラーを8g計量し、8回に分けて投入し混錬した。シラン処理ガラスフィラーを投入後、混錬時間が計30分となるように混錬し、均一なペーストとした。
作製したペーストを7g計量し、下記の表1の通りに後添加成分を加え、ヘラでなじませた。その後、自転公転ミキサーを用いて、800rpmにて3分間混錬し、フロアブル性状コンポジットレジンを得た。
BPE-80N:ビスフェノールAポリエトキシメタクリレート
NPG:ネオペンチルグリコールジメタクリレート
DCP:トリシクロデカンジメタノールジメタクリレート
CQ:カンファーキノン
EPA:p-ジメチルアミノ安息香酸エチル
BHT:6-tert-ジブチル-2,4-キシレノール
MTMAC:2-(メタクリロイルオキシ)エチルトリメチルアンモニウムクロライド
DADMAC:ジアリルジメチルアンモニウムクロライド
UDMA:ジ-2-メタクリロイルオキシエチル-2,2,4-トリメチルヘキサメチレンジカルバメート
得られたフロアブルコンポジットレジンのペーストをアクリル板の表面にまんべんなく塗布して直径15mm、厚み1mmの円盤型の試験片を作製し(図1、図2)、光照射器(ジーシー社製、G-ライトプリマII Plus)を用いて、試験片の表と裏の両面に10秒照射を9回ずつ行い、硬化体を作製し、これを試験体とした(図3)。変角光度計(村上色彩技術研究所製)を用いて、±90の測定範囲条件において、光散乱特性(光散乱性)を評価した。評価基準は以下の通りである。
良:透過光強度が初めて10%以下になる測定角度が±30の範囲外である
不可:透過光強度が初めて10%以下になる測定角度が±30の範囲内である
上述の光散乱特性の試験で得られた試験体(図3)について、ヘイズメーター(日本電色工業社製)を用いて、全光線透過率(T.T)を測定し、透明性を評価した。透明性の評価は、全光線透過率(T.T)が35%以上となるものを良(透明性がある)と判定した。
得られたフロアブルコンポジットレジンのペーストを、上述の光散乱特性の試験と同じ条件でアクリル板の表面に塗布し(図1、図2)、その外観を確認し、流動性を評価した。評価基準は、以下の通りである。
良:フロアブル性状(流動性がある)
不可:パテ性状(流動性がない)
光散乱特性の試験で得られた試験体(図3)について、外観評価を行った。外観評価では、作製した硬化体について、目視で確認可能な凹凸及び明らかな白濁を確認した(図3)。審美性の評価基準は、以下の通りである。なお、審美性の評価が不可の場合でも、上述の透明性の評価が良であれば、歯科用組成物としては良好なものと評価した。
良:凹凸及び白濁の何れもない
不可:凹凸及び/又は白濁がある
20 フロアブルコンポジットレジン
30 第1の重合性単量体
40 第2の重合性単量体が第1の溶媒に溶解している溶液
Claims (8)
- 第1の成分の中に、第2の成分が分散している歯科用組成物を製造する方法であって、
前記第1の成分は、液体である第1の重合性単量体を含むペーストであり、
前記第2の成分は、前記第1の重合性単量体が不溶な溶媒を含み、
前記第1の成分と、前記第2の成分を混合する工程を含む、
歯科用組成物の製造方法。 - 前記第1の成分は、さらに疎水性フィラーを含む、
請求項1に記載の歯科用組成物の製造方法。 - 前記第2の成分は、さらに固体である第2の重合性単量体を含み、
前記第2の重合性単量体は、前記溶媒に可溶である、
請求項1又は2に記載の歯科用組成物の製造方法。 - 前記工程は、前記第2の重合性単量体を前記溶媒に溶解させて溶液を得る工程と、
前記溶液と、前記第1の成分を混合する工程と、を含む、
請求項3に記載の歯科用組成物の製造方法。 - 前記歯科用組成物は、フロアブルコンポジットレジンである、
請求項1乃至4の何れか1項に記載の歯科用組成物の製造方法。 - 請求項1乃至5の何れか1項に記載の製造方法によって得られる、
歯科用組成物。 - 第1の成分の中に、第2の成分が分散している歯科用組成物であって、
前記第1の成分は、液体である第1の重合性単量体を含むペーストであり、
前記第2の成分は、前記第1の重合性単量体が不溶な溶媒を含む、
歯科用組成物。 - 前記第2の成分は、さらに固体である第2の重合性単量体を含み、
第2の重合性単量体は、前記溶媒に可溶である、
請求項7に記載の歯科用組成物。
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