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WO2025126917A1 - Composition dentaire - Google Patents

Composition dentaire Download PDF

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Publication number
WO2025126917A1
WO2025126917A1 PCT/JP2024/042807 JP2024042807W WO2025126917A1 WO 2025126917 A1 WO2025126917 A1 WO 2025126917A1 JP 2024042807 W JP2024042807 W JP 2024042807W WO 2025126917 A1 WO2025126917 A1 WO 2025126917A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
monomer
dental composition
acrylate
mass
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2024/042807
Other languages
English (en)
Japanese (ja)
Inventor
亮 松浦
瑛里 石黒
芳徳 北原
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JFE Chemical Corp
Kuraray Noritake Dental Inc
Original Assignee
JFE Chemical Corp
Kuraray Noritake Dental Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JFE Chemical Corp, Kuraray Noritake Dental Inc filed Critical JFE Chemical Corp
Publication of WO2025126917A1 publication Critical patent/WO2025126917A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
    • A61K6/833—Glass-ceramic composites
    • 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
    • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a dental composition.
  • dental compositions include dental filling and restorative materials such as dental composite resins, self-adhesive dental composite resins, and dental cements that are used to fill cavities formed in teeth or repair such cavities, as well as dental core construction materials that are used to plug or cover non-vital teeth with large defects to restore them to the shape of an abutment tooth.
  • dental compositions containing a polymerizable monomer having a bisphenol A skeleton, such as 2,2-bis[4-(meth)acryloyloxypolyethoxyphenyl]propane have been widely used. It is also known to add a filler to a dental composition for the purposes of adjusting the paste properties, imparting X-ray contrast properties to the cured product, improving the mechanical strength of the cured product, and the like.
  • conventional polymerizable monomers having a bisphenol A skeleton do not have a sufficiently high refractive index, and therefore dental compositions containing conventional polymerizable monomers having a bisphenol A skeleton have a large refractive index difference from the filler, which tends to cause light scattering and therefore tends to result in a small photocuring depth. If the photocuring depth is small, it becomes difficult to sufficiently cure the dental composition, which creates the problem of making it difficult to improve the mechanical strength of the cured product. For this reason, there is a demand for dental compositions that have a larger photocuring depth and can produce a cured product with high mechanical strength.
  • Patent Document 9 does not relate to dental filling and restorative materials or dental core construction materials, it describes a stereolithography resin composition used for dental occlusal splints and the like, which contains an ⁇ , ⁇ -unsaturated double bond group-containing compound having a nitrogen atom-containing cyclic structure (a), a (meth)acrylic acid ester compound having a predetermined normal pressure boiling point, a carbocyclic group, and no nitrogen-containing heterocyclic group, and a photopolymerization initiator.
  • Patent Document 9 has technical issues of odor, moldability, toughness, and water resistance, and does not consider light scattering when a filler is contained in the resin composition. Patent Document 9 does not describe or suggest how to ensure a sufficiently large photocuring depth while containing a high proportion of filler in the resin composition.
  • JP 2013-60373 A Patent No. 5008852 International Publication No. 2019/107322 Patent No. 5819415 Special Publication No. 2010-506931 Patent No. 6458034 International Publication No. 2020/218446 International Publication No. 2021/132463 International Publication No. 2020/129736
  • an object of the present invention is to provide a dental composition which can give a cured product having high mechanical strength, little polymerization shrinkage, large photocuring depth, and high surface hardness.
  • the present invention encompasses the following inventions.
  • a dental composition comprising a monomer (A), a polymerization initiator (B), and a filler (C),
  • the monomer (A) contains a monomer (A-1) represented by the following formula (1) and a monomer (A-2) other than the monomer (A-1),
  • a dental composition comprising a filler (C) in an amount of 50 to 90% by mass, based on a total mass of the dental composition being 100% by mass.
  • R1 represents a hydrogen atom or a methyl group
  • R2 represents a divalent hydrocarbon group
  • R3 represents an oxygen atom or a sulfur atom.
  • R4 and R5 each independently represent a halogen atom, an alkyl group, or an alkoxy group, m represents 0 or 1, n represents 0 or 1, p represents 0 to 3, and q represents 0 to 4. However, when m is 0, n is 0. When p is 2 or greater, a plurality of R 4s are the same atom or group or different atoms or groups. When q is 2 or more, the multiple R 5s are the same atom or group or different atoms or groups. [2] The dental composition according to the above [1], containing 1 to 80 parts by mass of the monomer (A-1) in 100 parts by mass of the total mass of the monomer (A-1) and the monomer (A-2).
  • the monomer (A-2) includes a monomer having a (meth)acryloyl group.
  • the content of a monomer having a bisphenol A skeleton is more than 0% by mass and not more than 30% by mass, or the dental composition does not contain a monomer having a bisphenol A skeleton.
  • the present invention provides a dental composition that produces a cured product with a large photocuring depth, high mechanical strength, low polymerization shrinkage stress, and high surface hardness.
  • the upper and lower limit values of the numerical ranges can be appropriately combined.
  • the numerical values of each symbol in the formula can also be appropriately combined.
  • the lower limit and upper limit described in stages for a numerical range can be combined independently.
  • a description of "preferably 10 to 90, more preferably 30 to 60" for the same item can be combined with a “preferable lower limit (10)” and a “more preferable upper limit (60)” to give “10 to 60.”
  • the upper limit value may not be specifically specified and only the lower limit value may be specified as “10 or more” or “30 or more”
  • the lower limit value may not be specifically specified and only the upper limit value may be specified as "90 or less” or "60 or less.”
  • a numerical range is simply stated as “10 to 90" it indicates a range of 10 or more and 90 or less.
  • p represents 0 to 3
  • q represents 0 to 4.
  • a plurality of R 4s are each the same atom or group or different atoms or groups.
  • a plurality of R 5s are each the same atom or group or different atoms or groups.
  • R 1 , R 2 , R 3 , m, and n have the same meanings as those defined in the above formula (1), and the preferred meanings are also the same as those described above.
  • the monomer (A-1) is more preferably a monomer (A-1b) represented by the following formula (3).
  • the monomer (A-1) is more preferably a monomer (A-1c) represented by the following formula (4).
  • R 1 , R 2 and m are defined as same as those in the above formula (1).
  • the monomer (A-1) is preferably 1-naphthylmethyl (meth)acrylate or 2-naphthylmethyl (meth)acrylate from the viewpoint of increasing mechanical strength and surface hardness, and more preferably 1-naphthylmethyl (meth)acrylate from the viewpoint of preventing a decrease in photocuring depth and further reducing polymerization shrinkage stress, and particularly preferably 1-naphthylmethyl methacrylate.
  • Monomer (A-2) is a compound different from monomer (A-1), that is, a polymerizable monomer having a structure different from that of compound (1).
  • the monomer (A-2) preferably contains a monomer having a urethane bond, and more preferably a polyfunctional polymerizable monomer containing a urethane bond.
  • the monomer (A-2) preferably contains a monomer having a (meth)acryloyl group, and from the viewpoint of further enhancing the curability, it is more preferable that the monomer (A-2) contains a monomer having a plurality of (meth)acryloyl groups.
  • Examples of monofunctional (meth)acrylate polymerizable monomers include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, propylene glycol mono(meth)acrylate, glycerol mono(meth)acrylate, erythritol mono(meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, isobutyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate,
  • Examples of monofunctional (meth)acrylamide polymerizable monomers include (meth)acrylamide, N-(meth)acryloylmorpholine, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-di-n-propyl(meth)acrylamide, N,N-di-n-butyl(meth)acrylamide, N,N-di-n-hexyl(meth)acrylamide, N,N-di-n-octyl(meth)acrylamide, and N,N-di-2-ethylhexyl(meth)acrylamide.
  • Examples of such compounds include N-hydroxyethyl(meth)acrylamide, N,N-bis(2-hydroxyethyl)acrylamide, N-(meth)acryloylcarbazole, N-methyl-N-phenyl(meth)acrylamide, N-(meth)acryloylmorpholine, N-piperidinyl acrylamide, N-tetramethylpiperidinyl acrylamide, N-2-methylpiperidinyl acrylamide, N-3-methylpiperidinyl acrylamide, and N-4-methylpiperidinyl acrylamide. These compounds may be used alone or in combination of two or more.
  • the structure of the polyfunctional polymerizable monomer is not particularly limited, but a polyfunctional polymerizable monomer containing a urethane bond is preferred because of its excellent curing properties.
  • examples of the polyfunctional polymerizable monomer include polyfunctional polymerizable monomers of aromatic compounds and polyfunctional polymerizable monomers of aliphatic compounds, but polyfunctional polymerizable monomers of aromatic compounds are preferred because they make it easier to obtain good curing properties.
  • hydroxy(meth)acrylate compounds include hydroxy(meth)acrylate compounds such as N,N-bis(2-hydroxyethyl)(meth)acrylamide, 2-hydroxy-3-acryloyloxypropyl(meth)acrylate, 2,2-bis[4-[3-(meth)acryloyloxy-2-hydroxypropoxy]phenyl]propane, 1,2-bis[3-(meth)acryloyloxy-2-hydroxypropoxy]ethane, pentaerythritol tri(meth)acrylate, and dipentaerythritol tri- or tetra(meth)acrylate.
  • hydroxy(meth)acrylate compounds such as N,N-bis(2-hydroxyethyl)(meth)acrylamide, 2-hydroxy-3-acryloyloxypropyl(meth)acrylate, 2,2-bis[4-[3-(meth)acryloyloxy-2-hydroxypropoxy]phenyl]propane, 1,2-bis[3-(meth)acrylo
  • the polymerization initiator (B) can be selected from polymerization initiators used in general industry, and among them, polymerization initiators used in dental applications are preferably used, and among them, photopolymerization initiators are particularly preferred.
  • the polymerization initiator (B) may be used alone or in combination of two or more kinds.
  • examples of the acylphosphine oxides include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylmethoxyphenylphosphine oxide, 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide, 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide, and benzoyldi(2,6-dimethylphenyl)phosphonate and salts thereof (for example, sodium salt, potassium salt, ammonium salt).
  • bisacylphosphine oxides include bis(2,6-dichlorobenzoyl)phenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-1-naphthylphosphine oxide, bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and bis(2,6-dimethoxybenzoyl)-2,5-dimethylphenylphosphine oxide.
  • phenylphosphine oxide bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,5,6-trimethylbenzoyl)-2,4,4-trimethylpentylphosphine oxide and salts thereof (e.g., sodium salts, potassium salts, ammonium salts), sodium phenyl(2,4,6-trimethylbenzoyl)phosphinate, lithium phenyl(2,4,6-trimethylbenzoyl)phosphinate, sodium bis(2,4,6-trimethylbenzoyl)phosphinate, and lithium bis(2,4,6-trimethylbenzoyl)phosphinate.
  • salts thereof e.g., sodium salts, potassium salts, ammonium salts
  • sodium phenyl(2,4,6-trimethylbenzoyl)phosphinate sodium phenyl(2,4,6-trimethylbenzoyl)phosphinate
  • 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylmethoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and the sodium salt of 2,4,6-trimethylbenzoylphenylphosphine oxide are particularly preferred.
  • sodium bis(2,4,6-trimethylbenzoyl)phosphinate and lithium bis(2,4,6-trimethylbenzoyl)phosphinate are preferred from the standpoint of adhesion to tooth structure.
  • ketals examples include benzyl dimethyl ketal and benzyl diethyl ketal.
  • ⁇ -diketones examples include diacetyl, benzil, camphorquinone, 2,3-pentadione, 2,3-octadione, 9,10-phenanthrenequinone, 4,4'-oxybenzil, and acenaphthenequinone.
  • camphorquinone is particularly preferred because it has a maximum absorption wavelength in the visible light range.
  • Examples of coumarin compounds include those described in JP-A-9-3109 and JP-A-10-245525, specifically 3,3'-carbonylbis(7-diethylaminocoumarin), 3-(4-methoxybenzoyl)coumarin, 3-thienylcoumarin, 3-benzoyl-5,7-dimethoxycoumarin, 3-benzoyl-7-methoxycoumarin, 3-benzoyl-6-methoxycoumarin, 3-benzoyl-8-methoxycoumarin, 3-benzoylcoumarin, 7-methoxy-3-(p-nitrobenzoyl)coumarin, 3-(p-nitrobenzoyl)coumarin, 3,5-carbonylbis(7-methoxycoumarin), 3-benzoyl-6-bromocoumarin, 3,3'-carbonylbiscoumarin, 3- Benzoyl-7-dimethylaminocoumarin, 3-benzoylbenzo[f]coumarin, 3-carboxycoumarin, 3-carboxy-7-methoxycoumarin,
  • 3,3'-carbonylbis(7-diethylaminocoumarin) and 3,3'-carbonylbis(7-dibutylaminocoumarin) are particularly suitable.
  • (bis)acylphosphine oxides, ⁇ -diketones, and coumarin compounds have excellent photopolymerization initiation ability in the visible and near-ultraviolet regions, so polymerization can be initiated using a light source (e.g., a halogen lamp, a light-emitting diode (LED), or a xenon lamp).
  • a light source e.g., a halogen lamp, a light-emitting diode (LED), or a xenon lamp.
  • the cured product of the dental composition preferably has a high surface hardness in order to easily prevent damage caused by contact with foreign matter. More specifically, the surface of the cured product obtained by irradiating the dental composition with light is mirror-polished, and the Vickers hardness value of the surface measured using a microhardness tester is preferably 30 Hv or more, more preferably 35 Hv or more, even more preferably 40 Hv or more, and even more preferably 45 Hv or more. There is no particular upper limit, but from the viewpoint of handleability of the paste, it is, for example, 100 Hv or less. In other words, the Vickers hardness of the dental composition is preferably 30 to 100 Hv.
  • ⁇ Filler 3> A commercially available surface-treated SiO 2 —ZrO 2 agglomerated filler (SG-SZ200G151CMP8, average particle size of primary particles: 200 nm, average particle size of secondary particles: 5.2 ⁇ m, refractive index: 1.51, manufactured by Sukyung AT Co., Ltd.) was used as filler 3 .
  • a dental adhesive product name "Clearfil (registered trademark) Megabond (registered trademark) 2 Bond", manufactured by Kuraray Noritake Dental Co., Ltd.
  • a dental adhesive product name "Clearfil (registered trademark) Megabond (registered trademark) 2 Bond", manufactured by Kuraray Noritake Dental Co., Ltd.
  • Pencure 2000 manufactured by Morita Co., Ltd.
  • a dental visible light irradiator (PenCure 2000, manufactured by Morita Co., Ltd.) was used to irradiate the paste from above and below in standard mode at five locations on each side for 10 seconds each (50 seconds total for each side) through the slide glass to harden the paste and obtain a hardened product.
  • Five hardened products were prepared for each Example and Comparative Example.
  • ⁇ Vickers hardness> The dental composition of each Example and Comparative Example was filled into a syringe, and a polytetrafluoroethylene mold with a hole of 10 mm ⁇ 5 mm was filled with the paste and pressed with a polypropylene film.
  • the clean smooth surface of the hardened body was polished under dry conditions using #1500 abrasive paper, and finally mirror-polished with diamond paste to prepare a test piece.
  • This test piece was subjected to a load of 200 g for 10 seconds using a microhardness tester (HM-221, Mitutoyo Corporation) to measure the Vickers hardness (Hv).
  • HM-221, Mitutoyo Corporation a microhardness tester
  • Hv Vickers hardness
  • the measurement was performed at a total of five points, one at the center of the hardened body and four points around it, and the arithmetic average value of the measured values at these five points was taken as the Vickers hardness of the dental composition of each Example and Comparative Example.
  • the cured products obtained by curing the dental compositions of Examples 1 to 11 had high bending strength and high Vickers hardness.
  • the dental compositions of Examples 2, 6, 8, and 9 gave cured products with high bending strength exceeding 130 MPa.
  • the cured products obtained by curing the dental compositions of Examples 5, 6 and 9 had a high flexural modulus of elasticity of 8.7 GPa or more.
  • the cured products obtained by curing the dental compositions of Examples 2, 3, and 7 to 9 had high Vickers hardness of more than 40 Hv.
  • the dental compositions of Examples 1 to 4, 7, 10 and 11 were cured to give cured products having a polymerization shrinkage stress of less than 8.0 MPa.
  • the cured products obtained by curing the dental compositions of Comparative Examples 1 to 4 not containing the monomer (A-1) were inferior in at least one of the properties of Vickers hardness and polymerization shrinkage stress to the cured products of the dental compositions of the Examples.
  • Comparative Example 1 was inferior to all the Examples in Vickers hardness
  • Comparative Example 4 was inferior to all the Examples in polymerization shrinkage stress.
  • the dental compositions of Comparative Examples 2 and 3 did not contain the monomer (A-1), the cured products were brittle and it was difficult to measure the polymerization shrinkage stress, compared with the dental composition of Example 4.
  • the Vickers hardness of these cured products was significantly inferior.
  • the dental composition of Comparative Example 5 had a filler (C) content of less than 50%, and therefore had a lower flexural modulus and Vickers hardness than the dental compositions of the Examples. In addition, the cured product was brittle, making it difficult to measure the polymerization shrinkage stress.

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention concerne une composition dentaire à partir de laquelle peut être obtenu un produit durci ayant une grande profondeur photodurcissable, une résistance mécanique élevée, une faible contrainte de retrait par polymérisation et une dureté de surface élevée. La composition dentaire comprend un monomère (A), un initiateur de polymérisation (B) et une charge (C). Le monomère (A) comprend un monomère (A-1) représenté par la formule (1) et un monomère (A-2) qui est autre que le monomère (A-1). La charge (C) est comprise entre 50 et 90% en masse dans 100% en masse de la composition dentaire. [Les symboles dans la formule (1) sont tels que définis dans la description de la présente demande.]
PCT/JP2024/042807 2023-12-12 2024-12-04 Composition dentaire Pending WO2025126917A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2023209300 2023-12-12
JP2023-209300 2023-12-12

Publications (1)

Publication Number Publication Date
WO2025126917A1 true WO2025126917A1 (fr) 2025-06-19

Family

ID=96057321

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2024/042807 Pending WO2025126917A1 (fr) 2023-12-12 2024-12-04 Composition dentaire

Country Status (1)

Country Link
WO (1) WO2025126917A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010046266A (ja) * 2008-08-21 2010-03-04 Tokuyama Dental Corp 歯列矯正用接着材
JP2021088150A (ja) * 2019-12-05 2021-06-10 クラレノリタケデンタル株式会社 光造形用樹脂組成物
JP2021523256A (ja) * 2018-05-04 2021-09-02 アライン テクノロジー， インコーポレイテッドＡｌｉｇｎ Ｔｅｃｈｎｏｌｏｇｙ，Ｉｎｃ． 重合可能なモノマー及び其れ等を重合する方法
WO2022230909A1 (fr) * 2021-04-26 2022-11-03 クラレノリタケデンタル株式会社 Kit pour obturation dentaire

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010046266A (ja) * 2008-08-21 2010-03-04 Tokuyama Dental Corp 歯列矯正用接着材
JP2021523256A (ja) * 2018-05-04 2021-09-02 アライン テクノロジー， インコーポレイテッドＡｌｉｇｎ Ｔｅｃｈｎｏｌｏｇｙ，Ｉｎｃ． 重合可能なモノマー及び其れ等を重合する方法
JP2021088150A (ja) * 2019-12-05 2021-06-10 クラレノリタケデンタル株式会社 光造形用樹脂組成物
WO2022230909A1 (fr) * 2021-04-26 2022-11-03 クラレノリタケデンタル株式会社 Kit pour obturation dentaire

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