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CN-121987502-A - Polymerizable dental composition

CN121987502ACN 121987502 ACN121987502 ACN 121987502ACN-121987502-A

Abstract

The present invention relates to a polymerizable dental composition comprising a specific monomer system comprising at least a specific high viscosity performance monomer and a specific low viscosity diluent monomer having a similar refractive index. The invention also relates to the use of this specific monomer system for the preparation of a crosslinked dental composition. Finally, the invention relates to the use of specific compounds in stabilizing polymeric dental compositions.

Inventors

  • T. Teller Scheler
  • Q.Dai
  • F. Sebastian

Assignees

  • 登士柏德萃有限公司
  • 登士柏西诺德公司

Dates

Publication Date
20260508
Application Date
20251104
Priority Date
20241104

Claims (10)

  1. 1. A polymerizable dental composition comprising (A) From 10 to 99% by weight, based on the total weight of the dental composition, of a homogeneous mixture of polymerizable monomers comprising (A1) From 5 to 99.5% by weight, based on the total weight of the mixture, of a first polymerizable component comprising one or more diluent compounds of formula (I): (I) wherein R may be the same or different and independently of one another represent a hydrogen atom or a C 1-4 alkyl group which may be substituted by one or more fluorine atoms, and (A2) 0.5 to 90% by weight, based on the total weight of the mixture, of one or more performance agent compounds of formula (II): (II) Wherein R 1 , which may be identical or different, are selected independently of one another from the following formulae (II-a) or (II-b): Wherein R 2 represents a hydrogen atom or a C 1-4 alkyl group which may be substituted by one or more fluorine atoms, and (A3) An optional third polymerizable component; (b) Polymerization initiator system, and (C) 10 to 90% by weight of a particulate filler.
  2. 2. The polymerizable dental composition according to claim 1, wherein the content of the third polymerizable component (a 3) is from 0.001 to 90 wt. -%, preferably from 0.01 to 70 wt. -%, more preferably from 0.01 to 60 wt. -%, in particular from 0.01 to 40 wt. -%, of the third polymerizable component, based on the total weight of the mixture.
  3. 3. The polymerizable dental composition according to claim 1 or 2, further comprising 0.001 to 10 wt. -%, preferably 0.01 to 7 wt. -%, particularly 0.05 to 6 wt. -%, especially 0.05 to 5 wt. -%, based on the total weight of the dental composition, of at least one UV stabilizer, preferably wherein the UV stabilizer is a compound of the following formula (III): (III) Wherein the method comprises the steps of R' is a hydrogen atom or a C 1-4 alkyl group, and L is a single bond or a divalent linker.
  4. 4. The polymerizable dental composition according to any of the preceding claims, further comprising from 0.0001 to 10 wt. -%, preferably from 0.001 to 7 wt. -%, in particular from 0.005 to 6 wt. -%, especially from 0.005 to 5 wt. -% of at least one polymerization inhibitor, based on the total weight of the dental composition.
  5. 5. The polymerizable dental composition of any of the preceding claims further comprising from 0.0001 to 1 wt% of at least one pigment based on the total weight of the dental composition.
  6. 6. The polymerizable dental composition according to any of the preceding claims, wherein the particulate filler comprises glass.
  7. 7. The polymerizable dental composition according to any of the preceding claims, wherein the first polymerizable component comprises at least two compounds of formula (I), preferably wherein the two or more compounds are enantiomers, diastereomers and structural isomers, and/or Wherein the one or more compounds of formula (I) comprise or consist of compounds of the following formulae (I-a) and/or (I-b): (I-a) (I-b) wherein R may be the same or different and are independently as defined in claim 1, and/or Wherein R represents a hydrogen atom, and/or Wherein the ratio n (a1) /n (a2) of the refractive index of component (a 1) to the refractive index of component (a 2) is in the range of 0.95 to 1.05, and/or Wherein the third polymerizable component comprises one or more polymerizable monomers selected from bisphenol a-glycidyl methacrylate (BisGMA), urethane Dimethacrylate (UDMA), and ethoxylated bisphenol a dimethacrylate (BisEMA), polycarbonate urethane dimethacrylate (PCUDMA).
  8. 8. The polymerizable dental composition according to any one of claims 3 to 7, wherein in the compound of formula (III), R' is a hydrogen atom or a methyl group, and/or Wherein L is alkylene or polyoxyalkylene, and/or Containing 0.001 to 5% by weight of a compound of formula (III), based on the total weight of the dental composition, and/or Wherein the compound of formula (III) is a compound of formula (III-a): (III-a) And/or Comprising a particulate filler in an amount of 40 to 90 wt% based on the total weight of the composition.
  9. 9. Use of a compound of the following formula (III) for stabilizing a polymerized dental composition: (III) Wherein the method comprises the steps of R' is a hydrogen atom or a C 1-4 alkyl group, and L is a divalent linker.
  10. 10. The use according to claim 9, wherein the compound of formula (III) is a compound of formula (III-a) below: (III-a)。

Description

Polymerizable dental composition Priority claim The present application claims priority from european application number 24210551.8 filed on month 4 of 2024, 11 and claims priority thereto, the entire contents of which are incorporated herein by reference. Technical Field The present invention relates to a polymerizable dental composition comprising a specific monomer system comprising at least a specific high viscosity performance monomer and a specific low viscosity diluent monomer having a similar refractive index. The invention also relates to the use of this specific monomer system for the preparation of a crosslinked dental composition. Finally, the invention relates to the use of specific compounds in stabilizing polymeric dental compositions. Background Polymerizable dental compositions comprising dental restorative materials are known. The universal composition mainly comprises polymerizable monomers, an initiator system, and other components depending on clinical use, such as particulate fillers, solvents, and UV stabilizers. Polymerizable monomers in dental restorative materials (e.g., dental composites) must meet a number of requirements. In addition to mechanical and rheological properties, optical properties must also be considered. Optimizing all these properties of dental materials simultaneously is a significant challenge. Any trade-off may lead to poor material properties. For example, high viscosity monomers and high filler contents are required in order to obtain high mechanical strength and stability. On the other hand, in order to obtain good handling properties while maintaining a high filler content, a low viscosity of the resin matrix is required. Thus, a diluent or reactive diluent may be used to reduce the viscosity of the dental restorative material. Combining high viscosity monomers as a performance agent with a diluent allows for adjusting the mechanical properties and viscosity of the dental material. However, it is difficult to adjust the rheological properties of the monomer mixture without changing the optical properties. Diluents or reactive diluents are low viscosity reactive monomers or oligomers added to the polymerizable dental composition for reducing its viscosity while still being able to chemically react with other components of the composition during polymerization. For example, ethylene Glycol Dimethacrylate (EGDMA) or triethylene glycol dimethacrylate (TEGDMA) is commonly used as a reactive diluent in polymerizable dental compositions. However, EGDMA or TEGDMA reduces the refractive index of the polymeric dental resin matrix, as for example the refractive index of polymeric TEGDMA is typically only about 1.46 to 1.48, which differs significantly from the refractive index of the dental filler material. Refractive index is an important property of dental materials because the refractive index of the polymerizable liquid should be matched to the dental filler to ensure that the optical properties of the dental composite match those of the natural tooth structure. US10,849,724 discloses in example 2a specific urethane monomer (UCDPMAA) with desirable properties as a performance agent. UCDPMAA are high-performance monomers, which have good mechanical properties after polymerization. However, UCDPMAA is highly viscous and prone to crystallization and is not suitable for use in pure form with dental materials. Disclosure of Invention According to a first aspect, the problem of the present invention is to provide a filler-containing polymerizable dental composition having an adjustable liquid viscosity and a substantially constant refractive index, which after polymerization matches the refractive index of the particulate filler (e.g. dental glass), providing natural tooth-like opacity after curing, good handling properties, sufficient mechanical stability, easy addition of other functions without affecting aesthetics, good biocompatibility and low risk of health problems. Furthermore, the problem of the present invention is to provide the use of a specific monomer system for the preparation of a crosslinked dental composition. The problem according to the first aspect is solved by a polymerizable dental composition comprising (A) From 10 to 99% by weight, based on the total weight of the dental composition, of a homogeneous mixture of polymerizable monomers comprising (A1) From 5 to 99.5% by weight, based on the total weight of the mixture, of a first polymerizable component comprising one or more diluent compounds of formula (I): (I) wherein R may be the same or different and independently of one another represent a hydrogen atom or a C 1-4 alkyl group which may be substituted by one or more fluorine atoms, and (A2) 0.5 to 90% by weight, based on the total weight of the mixture, of one or more performance agent compounds of formula (II): (II) Wherein R 1, which may be identical or different, are selected independently of one another from the following formulae (II-a)