Photopolymerizable and dual-curing dental materials based on thiourea derivatives

Patent metadata

Field	Value
Publication number	US-10195121-B2
Application number	US-201515127428-A
Country	US
Kind code	B2
Filing date	Mar 19, 2015
Priority date	Mar 20, 2014
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

Radically polymerizable dental material which contains as initiator for the radical polymerization a combination of a thiourea derivative and a bisacyldialkylgermanium compound.

First claim

The invention claimed is:

1. A radically polymerizable dental material which comprises an initiator for the radical polymerization, wherein the initiator comprises a combination of a thiourea derivative and a bisacyldialkylgermanium compound,
wherein the thiourea derivative is selected from methyl, ethyl, allyl, butyl, hexyl, octyl, benzyl, 1,1,3-trimethyl, 1,1-diallyl, 1,3-diallyl, 1-(2-pyridyl)-2-thiourea, acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, benzoyl thiourea or a mixture thereof; and
wherein said radically polymerizable dental material comprises as a polymerizable matrix a mixture of radically polymerizable monomers which comprises at least one highly viscous difunctional methacrylate which is selected from TMX-UDMA (an addition product of HEMA and hydroxypropyl methacrylate (HPMA) with α,α,α′,α′-tetramethyl-m-xylylene diisocyanate (TMXDI)) and 1,6-bis-[2-methacryloyloxyethoxycarbonylamino]-2,4,4-tri¬methylhexane (U DMA); at least one low-viscosity difunctional methacrylate which is selected from bismethacryloyloxymethyltricyclo[5.2.1]decane (TCDMA), glycerol dimethacrylate (GDMA) and/or decanediol-1,10-dimethacrylate (D3MA); and p-cumylphenoxyethylene glycol methacrylate (CMP-1E) as a low-volatile monomethacrylate.

2. The dental material according to claim 1 , which comprises as the bisacyldialkylgermanium compound, bisbenzoyldiethylgermanium, bisbenzoyldimethylgermanium, bisbenzoyldibutylgermanium, bis(4-methoxybenzoyl)dimethylgermanium, bis(4-methoxybenzoyl)diethylgermanium or a mixture thereof.

3. The dental material according to claim 1 , which additionally comprises a hydroperoxide.

4. The dental material according to claim 3 , which comprises as the hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-butyl hydroperoxide, cumene hydroperoxide, pinane hydroperoxide, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, t-amyl hydroperoxide or a mixture thereof.

5. The dental material according to claim 1 , which additionally comprises organic or inorganic particulate filler.

6. The dental material according to claim 5 , which comprises filler with a maximum particle size of less than 600 nm.

7. The dental material according to claim 1 , which comprises
(a) 2.0-20 wt.-% of said low-volatile monomethacrylate,
(b1) 5.0-25 wt.-% of said highly viscous dimethacrylates,
(b2) 5-30 wt.-% of said low-viscosity dimethacrylates,
(e) 0.01-4.0 wt.-% of said thiourea derivative,
(g) 0.001-1.0 wt.-% of said bisacyldialkylgermanium compound,
said composition further comprising
(c) 0-15 wt.-% of one or more acid-group-containing adhesive monomers,
(d) 20-90 wt.-% filler(s),
(f) 0-3.0 wt.-% hydroperoxide(s),
(h) 0.1-5.0 wt.-% additive(s).

8. The dental material according to claim 1 , which further comprises 10 to 100 ppm of a redox catalyst.

9. The dental material according to claim 1 , which is free from TEGDMA and bis-GMA.

10. The dental material according to claim 1 , which is free from amines.

11. A method of using of a dental material according to claim 1 as dental cement, filling composite, veneering material, as materials for preparing inlays, onlays, crowns or bridges comprising preparing the ingredients according to claim 7 and applying the ingredients as a dental cement, filling composite, veneering material.

12. The dental material according to claim 1 , which comprises
(a) 5-15 wt.-% of said low-volatile monomethacrylate,
(b1) 5-15 wt.-% of said highly viscous dimethacrylates,
(b2) 10-20 wt.-% of said low-viscosity dimethacrylates,
(e) 0.1-2.0 wt.-% of said thiourea derivative,
(g) 0.005-0.5 wt.-% of said bisacyldialkylgermanium compound,
said composition further comprising
(c) 0-10 wt.-% of one or more acid-group-containing adhesive monomers,
(d) 40-80 wt.-% filler(s),
(f) 0.1-2.0 wt.-% hydroperoxide(s),
(h) 0.1-2.0 wt.-% additive(s).

13. The dental material according to claim 1 , which further comprises 20 to 80 ppm of a redox catalyst.

14. The dental material according to claim 1 , which comprises 30 to 80 ppm of a redox catalyst.

15. The dental material according to claim 1 , which comprises TMX-UDMA.

16. The dental material according to claim 1 , which comprises CMP-1E.

17. The dental material according to claim 1 , which comprises TMX-UDMA and CMP-1E.

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Burtscher Peter
• Gianasmidis Alexandros

Classifications

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/20

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title

• A61K6/61 Primary

  Cationic, anionic or redox initiators · CPC title

• A61K6/64 Primary

  Thermal radical initiators · CPC title

• A61K6/889

  Polycarboxylate cements; Glass ionomer cements · CPC title