Dental materials based on low-viscosity radically polymerizable monomers with a high refractive index

Patent metadata

Field	Value
Publication number	US-10857073-B2
Application number	US-201816032382-A
Country	US
Kind code	B2
Filing date	Jul 11, 2018
Priority date	Jul 14, 2017
Publication date	Dec 8, 2020
Grant date	Dec 8, 2020

Abstract

Radically polymerizable, difunctional phenylene sulfide according to Formula I

in which X, Y independently of each other in each case are absent or are O or NR 6 , R 1 , R 2 independently of each other in each case are H, a linear or branched C 1 to C 10 alkyl radical, —OR 7 , —SR 8 , Cl or Br, R 3 is absent or is a C 1 -C 10 alkylene radical which can be interrupted by O or S, R 4 is absent or is a C 1 -C 10 alkylene radical which can be interrupted by O or S, wherein R 3 and R 4 cannot be absent at the same time, R 5 is H or a C 1 -C 5 alkyl radical, R 6 , R 7 , R 8 independently of each other in each case are H or a linear or branched C 1 to C 10 alkyl radical, a, b, c, d independently of each other in each case are 0 or 1 and e is 1 or 2.

First claim

The invention claimed is:

1. A dental material, comprising at least one radically polymerizable, difunctional phenylene sulfide according to Formula I,

in which
X, Y independently of each other in each case are absent or are 0 or NR 6 ,
R 1 , R 2 independently of each other in each case are H, a linear or branched C 1 to C 10 alkyl radical, —OR 7 , —SR 8 , Cl or Br,
R 3 is absent or is a C 1 -C 10 alkylene radical, which can be interrupted by O or S,
R 4 is absent or is a C 1 -C 10 alkylene radical, which can be interrupted by O or S,
R 5 is H or a C 1 -C 5 alkyl radical,
R 6 , R 7 , R 8 independently of each other in each case are H or a linear or branched C 1 to C 10 alkyl radical,
a, b, c, d independently of each other in each case are 0 or 1 and
e is 1 or 2,
at least one mono- or multifunctional (meth)acrylate, and
at least one filler in an amount of 65-85% of the dental material.

2. The dental material according to claim 1 , wherein the variables have the following meanings:
X, Y independently of each other in each case are absent or are 0,
R 1 , R 2 independently of each other in each case are H or Br, CH 3 , SCH 3 , OCH 3 ,
R 3 is absent or is a C 2 -C 4 alkylene radical,
R 4 is absent or is a C 1 -C 3 alkylene radical,
R 5 is H or CH 3 ,
a, b, c, d independently of each other in each case are 0 or 1, and
e is 1.

3. The dental material according to claim 1 , wherein the variables have the following meanings:
R 1 , R 2 independently of each other in each case are H or Br,
R 3 is dispensed with or is a C 2 -C 4 alkylene radical,
R 4 is dispensed with or is a C 1 -C 3 alkylene radical,
R 5 is H,
a, b, c, d in each case are 0, and
e is 1.

4. The dental material according to claim 1 , wherein the difunctional phenylene sulfide of Formula I has a viscosity of 3 Pas, measured using a capillary viscometer at a temperature of 23° C.

5. The dental material according to claim 4 , wherein the viscosity is in the range of 5 to 2,000 mPas, measured using a capillary viscometer at a temperature of 23° C.

6. The dental material according to claim 1 , wherein the difunctional phenylene sulfide of Formula I has a refractive index of more than 1.57, measured at 20° C. with the light of the yellow Na D line (λ=589 nm).

7. The dental material according to claim 6 , wherein the refractive index is in the range of from 1.575 to 1.75, measured at 20° C. with the light of the yellow Na D line (λ=589 nm).

8. The dental material according to claim 1 , which additionally contains at least one initiator for the radical polymerization, wherein the initiator comprises a photoinitiator.

9. The dental material according to claim 1 , wherein the at least one mono- or multifunctional (meth)acrylate comprises Bis-GMA, UDMA, TMX-UDMA, D 3 MA, TEGDMA, CMP-1E, TCP, SR-348c or a mixture thereof.

10. The dental material according to claim 1 , wherein the at least one filler comprises an organic, inorganic or organic-inorganic filler.

11. The dental material according to claim 10 , wherein the at least one filler comprises a barium or strontium aluminium borosilicate glass, pyrogenic silica, a mixed oxide of SiO 2 and ZrO 2 , ytterbium fluoride or a mixture thereof.

12. The dental material according to claim 1 , which contains
(a) 5 to 70 wt.-% of at least one difunctional phenylene sulfide according to Formula I,
(b) 0.1 to 3.0 wt.-% of at least one initiator for the radical polymerization,
(c) 10 to 50 wt.-% of at least one further radically polymerizable monomer, in each case relative to the total mass of the material, and
(d) 65 to 85 wt.-% filler.

13. The dental material according to claim 1 for therapeutic use as a dental cement, filling composite or veneering material.

14. A method of using the dental material according to claim 1 for the extraoral production or repair of dental restorations, prosthetics, artificial teeth, inlays, onlays, crowns or bridges comprising
3D printing the dental material into one or more of the dental restorations, prosthetics, artificial teeth, inlays, onlays, crowns or bridges.

15. A method of using a difunctional phenylene sulfide according to Formula I of claim 1 for the preparation of a dental material comprising
3D printing the difunctional phenylene sulfide according to Formula I into the dental material.

16. The dental material according to claim 4 , wherein the viscosity is in the range of 10 to 1,000 mPas, measured using a capillary viscometer at a temperature of 23° C.

17. The dental material according to claim 6 , wherein the refractive index is in the range of from 1.58 to 1.72, measured at 20° C. with the light of the yellow Na D line (λ=589 nm).

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Fischer Urs Karl
• Fässler Pascal

Classifications

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C07C321/30

  Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings · CPC title

• C08F228/02

  by a bond to sulfur · CPC title

• C08F2800/20

  as weight or mass percentages · CPC title

• A61K6/842 Primary

  Rare earth metals · CPC title