Compositions with controlled network structure

Patent metadata

Field	Value
Publication number	US-10342744-B2
Application number	US-201515325246-A
Country	US
Kind code	B2
Filing date	Jul 9, 2015
Priority date	Jul 11, 2014
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

Radically polymerizable dental material, which contains at least one compound of Formula I:

The material preferably additionally contains a radically polymerizable monomer, an initiator for the radical polymerization and filler. It is characterized by a low polymerization contraction stress.

First claim

The invention claimed is:

1. Radically polymerizable dental material, which contains at least one radically polymerizable monomer, at least one initiator for the radical polymerization and at least one compound of Formula I:

wherein the variables of Formula I have the following meanings:
A a saturated, linear aliphatic hydrocarbon residue with 1 to 12 carbon atoms which can be interrupted by one or more 1,4-phenylene groups, urethane groups or O and which can carry in the terminal position a polymerizable methacryloyloxy group,
X —COO— or —CON(R 10 )—, wherein R 10 is methyl, or is absent, wherein the bond to A takes place via O or N;
R 1 H,
L SO 2 R 3 , wherein R 3 is CH 3 or tolyl,
n 1 or 2.

2. Dental material according to claim 1 , wherein the variables of Formula I have the following meanings:
A a saturated, linear aliphatic hydrocarbon radical with 6 to 12 carbon atoms which can be interrupted by 1 to 3 O atoms,
X —COO—,
R 1 H,
L SO 2 R 3 , wherein R 3 is CH 3 or tolyl, n 1 or 2.

3. Dental material according to claim 1 , which contains at least one multifunctional (meth)acrylate or a mixtures of mono- and multifunctional (meth)acrylates.

4. Dental material according to claim 1 , which contains at least one filler.

5. Dental material according to claim 1 , which additionally contains at least one photoinitiator for the radical polymerization.

6. Dental material according to claim 1 , which contains
0.5 to 60 wt.-% of at least one compound of general formula I,
0.01 to 5.0 wt.-% initiator(s) for the radical polymerization, and optionally
5 to 80 wt.-% multifunctional (meth)acrylate(s), in each case relative to the total mass of the dental material.

7. Dental material according to claim 6 , which has the following composition:
(a) 5 to 80 wt.-% multifunctional (meth)acrylate(s),
(b) 0.01 to 5.0 wt.-% initiator(s),
(c) 0.5 to 60 wt.-% of at least one compound of general formula I,
(d) 0 to 50 wt.-% monofunctional (meth)acrylate(s),
(e) 0 to 90 wt.-% filler(s), and
(f) 0 to 5 wt.-% additive(s),
in each case relative to the total mass of the dental material.

8. Dental material according to claim 1 , which does not contain volatile mercaptans.

9. Dental material according to claim 8 for intraoral use to restore damaged teeth.

10. Dental material according to claim 9 for use as cement, filling composite or veneering material.

11. Method of using the dental material according to claim 1 comprising extraorally manufacturing or repairing dental restorations.

12. Method of using the dental material according to claim 11 wherein the dental restorations comprise inlays, onlays, crowns or bridges.

13. Method of using the compound of Formula (I), comprising defining the variables in claim 1 to reduce the polymerization shrinkage stress of dental materials.

14. Dental material according to claim 1 , which contains
1.0 to 50 wt.-% of at least one compound of general formula I,
0.1 to 5.0 wt.-% initiator(s) for the radical polymerization, and optionally
10 to 70 wt.-% multifunctional (meth)acrylate(s), in each case relative to the total mass of the dental material.

15. Dental material according to claim 1 , which contains
1.0 to 40 wt.-% of at least one compound of general formula I,
0.1 to 3.0 wt.-% initiator(s) for the radical polymerization, and optionally
10 to 60 wt.-% multifunctional (meth)acrylate(s), in each case relative to the total mass of the dental material.

16. Dental material according to claim 6 , which comprises:
(a) 10 to 70 wt.-% multifunctional (meth)acrylate(s),
(b) 0.1 to 5.0 wt.-% initiator(s),
(c) 1.0 to 50 wt.-% of at least one compound of general formula I,
(d) 0 to 40 wt.-% monofunctional (meth)acrylate(s),
(e) 5 to 90 wt.-% filler(s), and
(f) 0 to 3 wt.-% additive(s),
in each case relative to the total mass of the dental material.

17. Dental material according to claim 6 , which comprises:
(a) 10 to 60 wt.-% multifunctional (meth)acrylate(s),
(b) 0.1 to 3.0 wt.-% initiator(s),
(c) 1.0 to 40 wt.-% of at least one compound of general formula I,
(d) 0 to 30 wt.-% monofunctional (meth)acrylate(s),
(e) 0 to 80 wt.-% filler(s), and
(f) 0.2 to 3 wt.-% additive(s),
in each case relative to the total mass of the dental material.

18. Dental material according to claim 1 , which does not contain any mercaptans at all.

19. Dental material according to claim 1 , which does not contain other sulphur compounds.

Assignees

• Ivoclar Vivadent Ag
• Univ Wien Tech

Inventors

• Moszner Norbert
• Fischer Urs-Karl
• Lamparth Iris
• Burtscher Peter
• Liska Robert
• Gorsche Christian
• Seidler Konstanze
• Gauss Paul

Classifications

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/887 Primary

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

• C07C317/44

  having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton · CPC title

• C07C317/28

  with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton · CPC title

• C07C323/52

  the carbon skeleton being acyclic and saturated · CPC title