Search

EP-4736833-A1 - POLYMERIZABLE DENTAL COMPOSITION

EP4736833A1EP 4736833 A1EP4736833 A1EP 4736833A1EP-4736833-A1

Abstract

The present invention relates to a polymerizable dental composition comprising a specific monomeric system containing at least a specific high viscosity performer monomer and a specific low viscosity thinner monomer with similar refractive indices. The present invention also relates to the use of the specific monomeric system for the preparation of a crosslinked dental composition. Finally, the present invention relates to the use of a specific compound for stabilizing a polymerized dental composition.

Inventors

  • TRÖTSCHLER, Tobias
  • Qizhou, Dai
  • FREDRICH, Sebastian

Assignees

  • DENTSPLY SIRONA Inc.
  • Dentsply DeTrey GmbH

Dates

Publication Date
20260506
Application Date
20241104

Claims (10)

  1. A polymerizable dental composition comprising (a) 10 to 99 percent by weight based on the total weight of the dental composition of a homogenous mixture of polymerizable monomers, which comprises (a1) 5 to 99.5 percent by weight based on the total weight of the mixture of a first polymerizable component comprising one or more thinner compounds of the following formula (I): wherein the R, which may be the same or different, independently from each other 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 percent by weight based on the total weight of the mixture of one or more performer compounds of the following formula (II): wherein the R 1 which may be the same or different, independently from each other is selected from a group of the following formulas (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) optionally a third polymerizable component; (b) a polymerization initiator system, and (c) 10 to 90 percent by weight of a particulate filler.
  2. The polymerizable dental composition according to claim 1, wherein the third polymerizable component (a3) is contained in an amount of 0.001 to 90 percent by weight, preferably 0.01 to 70 percent by weight, more preferably 0.01 to 60 percent by weight, especially 0.01 to 40 percent by weight based on the total weight of the mixture, of a third polymerizable component.
  3. The polymerizable dental composition according to claim 1 or 2, which further comprises 0.001 to 10 percent by weight, preferably 0.01 to 7 percent by weight, particularly 0.05 to 6 percent by weight, especially 0.05 to 5 percent by weight 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): wherein R' is a hydrogen atom or a C 1-4 alkyl group, and L is a single bond or a divalent linker.
  4. The polymerizable dental composition according to any one of the preceding claims, which further comprises 0.0001 to 10 percent by weight, preferably 0.001 to 7 percent by weight, particularly 0.005 to 6 percent by weight, especially 0.005 to 5 percent by weight based on the total weight of the dental composition of at least one polymerization inhibitor.
  5. The polymerizable dental composition according to any one of the preceding claims, which further comprises 0.0001 to 1 percent by weight based on the total weight of the dental composition of at least one pigment.
  6. The polymerizable dental composition according to any one of the preceding claims wherein the particulate filler comprises a glass.
  7. The polymerizable dental composition according to any one 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 constitutional isomers; and/or wherein the one or more compounds of formula (I) comprise or consist of compounds of the following formula (I-a) and/or (I-b): wherein the R, which may be the same or different, independently are as defined in claim 1; and/or wherein R represents a hydrogen atom; and/or wherein the ratio of the refractive index of the component (a1) and the refractive index of component (a2) n (a1) / n (a2) 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. 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 an alkylene group or a polyoxyalkylene group; and/or which contains 0.001 to 5 percent by weight based on the total amount of the total weight of the dental composition a compound of formula (III); and/or wherein the compound of formula (III) is a compound of the following formula (III-a): and/or which comprises the particulate filler in an amount of from 40 to 90 percent by weight based on the total weight of the composition.
  9. A use of a compound of the following formula (III): wherein R' is a hydrogen atom or a C 1-4 alkyl group, and L is a divalent linker; for stabilizing a polymerized dental composition.
  10. The use according to claim 9, wherein the compound of formula (III) is a compound of the following formula (III-a):

Description

Field of the Invention The present invention relates to a polymerizable dental composition comprising a specific monomeric system containing at least a specific high viscosity performer monomer and a specific low viscosity thinner monomer with similar refractive indices. The present invention also relates to the use of the specific monomeric system for the preparation of a crosslinked dental composition. Finally, the present invention relates to the use of a specific compound for stabilizing a polymerized dental composition. Background of the Invention Polymerizable dental compositions including dental restorative materials are known. Generic compositions mainly contain polymerizable monomers, an initiator system, and further components such as particulate fillers, solvents and UV-stabilizer depending on the clinical use. Polymerizable monomers in dental restorative materials such as in dental composites must meet several requirements. In addition to the mechanical and rheological properties, also the optical properties must be taken into account. Simultaneously optimizing all these properties for a dental material is a major challenge. Any trade-off can result in poor performance of the material. For example, high viscosity monomers and a high filler content are required for high mechanical strength and stability. On the other hand, the viscosity of the resin matrix needs to be low for achieving good handling performance while keeping the filler content high. Accordingly, a thinner or reactive diluent may be used for reducing the viscosity of the dental restorative material. A combination of high viscosity monomers as performers and a thinner allows to adjust mechanical properties and viscosity for dental materials. However, it is difficult to adjust the rheological properties of the monomer mixture while not changing the optical properties at the same time. Thinners or reactive diluents are low-viscosity, reactive monomers or oligomers added to a polymerizable dental composition to reduce its viscosity while still being capable of chemically reacting with other components in the composition during the polymerization process. For example, ethylene glycol dimethacrylate (EGDMA) or triethylene glycol dimethacrylate (TEGDMA) are commonly used as reactive diluents in polymerizable dental compositions. However, EGDMA or TEGDMA reduce the refractive index of the polymerized dental resin matrix given that, for example, the refractive index of polymerized TEGDMA is typically only around 1.46 to 1.48 which is significantly different the refractive index of a dental filler material. The refractive index is an important property for dental materials in that the refractive index of the polymerizable liquid should match the dental filler for ensuring that the optical properties of dental composites match those of natural tooth structures. US 10,849,724 discloses in Example 2 a specific urethane monomer (UCDPMAA) having desirable properties as a performer. UCDPMAA is a high performing monomer yielding good mechanical performance after polymerization. However, UCDPMAA has a high viscosity with the tendency to crystallize, which is not suitable in neat form for dental materials. Summary of the Invention According to a first aspect, it is the problem of the present invention to provide a filler-containing polymerizable dental composition having adjustable viscosity of the liquid and an essentially constant refractive index matching the refractive index of a particulate filler such as a dental glass after polymerization, and providing a natural tooth-like opacity after curing, good handling properties, sufficient mechanical stability, easy incorporation of further functionality without disturbing the esthetics, good biocompatibility and low risk of health issues. Moreover, it is the problem of the present invention to provide a use of the specific monomeric 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) 10 to 99 percent by weight based on the total weight of the dental composition of a homogenous mixture of polymerizable monomers, which comprises (a1) 5 to 99.5 percent by weight based on the total weight of the mixture of a first polymerizable component comprising one or more thinner compounds of the following formula (I): wherein the R, which may be the same or different, independently from each other represent a hydrogen atom or a C1-4 alkyl group which may be substituted by one or more fluorine atoms; and(a2) 0.5 to 90 percent by weight based on the total weight of the mixture of one or more performer compounds of the following formula (II): wherein the R1 which may be the same or different, independently from each other is selected from a group of the following formulas (II-a) or (II-b): wherein R2 represents a hydrogen atom or a C1-4 alkyl group which may be substituted by one or more fluorine at